ST.

JOHN’S COLLEGE OF PHARMACEUTICAL SCIENCES & RESEARCH

KATTAPPANA SOUTH P.O, IDUKKI DIST ,

KERALA. PIN: 685515

(Affiliated to Kerala University of Health Sciences,Thrissur)

BACHELOR OF PHARMACY FOURTH SEMESTR

MEDICINAL CHEMISTRY I

PRACTICAL LAB MANUAL

STAFF IN-CHARGE:

KARTHIKA C THANKACHEN

Name:

Roll No:

Batch:
 1. ASSAY OF ASPIRIN

AIM:

To perform Assay of aspirin.

REFERENCE:

1. A textbook of Medicinal Chemistry-I,Pragi Arora,Varun Arora,Davinder Kumar,Page no:282,283.

2. Indian Pharmacopoeia Volume I 1996, Page No:69,70.
3. Pharmaceutical titrimetric analysis theory and practical,A.A Napoleon,Page No:11-17.
REQUIREMENTS:

Aspirin, Sodium hydroxide solution (0.5N),Hydrochloric acid (0.5N),Phenol red indicator, Burette, Conical flask,
Funnel, Beaker etc.

PROCEDURE:

a) STANDARDIZATION OF 0.5M HYDROCHLORIC ACID

Weighed accurately 0.75g of Anhydrous sodium carbonate previously heated at 2700C. Dissolve in 100 ml of
water and added 0.1ml of methyl red solution. Added the titrant slowly from the burette with constant stirring
until the solution becomes faintly pink.

Heated the [Link] and [Link] pink colour fades on heating continue this process until a faint pink
colour is no longer affected by continous boiling.

Each ml of 0.5M HCl = 0.026495g of Na2CO3

b) ASSAY OF ASPIRIN
Weighed accurately 1.5g of aspirin and dissolved in 15ml ethanol added 50ml of 0.5M sodium hydroxide boil
gently for 10 minutes, cool and titrated the excess alkali with 0.5M HCl using phenol red solution as indicator.
Perform a blank determination the difference between the titration represent the volume of sodium hydroxide
consumed.

Each ml of 0.05M NaOH = 0.04504g of C9H8O

 2. ASSAY OF PHENOBARBITONE

AIM :

To perform the Assay of Phenobarbitone.

REFERENCE:

1. A textbook of Medicinal Chemistry-I,Pragi Arora,Varun Arora,Davinder Kumar,Page no:282,283.

2. Indian Pharmacopoeia Volume III 2018,Page No:2899,2900.

REQUIREMENTS:

Sodium hydroxide,aldehyde free ethanol,benzoic acid,thymolphthalein solution, silver nitrate,pyridine and

ether,conical flask,burette,beaker,pipette etc.

PRINCIPILE:

Phenobarbitone is assayed by non-aqueous [Link] this method,drug is dissolved in the pyridine and titrated
with sodium hydroxide solution using thymolphthalein as an indicator.

O N O
C2H5
O N O N
C2H5
N
+ 2H2O
ONa
+ H
O
2NaOH
H

Phenobarbitone Sodium hydroxide Phenobarbitone sodium

PROCEDURE:

a) STANDARDISATION OF SODIUM HYDROXIDE SOLUTION

Actually weighed 0.6g of benzoic acid and dissolved it in a mixture of 30ml of ethanol and 6ml of water and
titrated with ethanolic sodium hydroxide solution using 0.2ml of thymolphthalein as indicator.
 b) ASSAY OF PHENOBARBITONE
Weighed and powdered 20 tablets. Weighed a quantity of the powder containing about 0.1g (100 mg ) of
phenobarbitone in 5ml of pyridine add 0.25 ml of thymolphthalein solution and 10 ml of silver nitrate pyridine
reagent and titrated with 0.1M ethanolic sodium hydroxide until a pure blue colour is obtained. Repeated the
operation without the substance under examination. The difference between the titrations represents the
amount of sodium hydroxide required.

Equivalent factor: 1ml of 0.1M ethanolic sodium hydroxide=0.01161g of C12H12N2O3

REPORT

The percentage purity of Phenobarbitone was found to be

CALCULATION

a) Standardization of 0.1M Sodium hydroxide solution

Molarity of NaOH= Weight (W)

[Link] of benzoic acid (122.12) X Volume (V)

Where,

W = Weight of benzoic acid (g)

V = Volume of NaOH solution consumed

b) Determination of Phenobarbitone
% purity of phenobarbitone = 0.01161 x V X Molarity(Calculated) x 100

Molarity (given) x W

Where,

Molarity (calculated) = Molarity obtained from step (a) V = Volume of Sodium hydroxide used

0.01161 is the equivalent factor Molarity (given) = 0.1M

W = weight of sample

REPORT:

The percentage purity of Phenobarbitone was found to be =

 3. ASSAY OF FUROSEMIDE

AIM:

To carry out the Assay of furosemide tablets.

REFERENCE:

1. A textbook of Medicinal Chemistry-I,Pragi Arora,Varun Arora,Davinder Kumar,Page no:288,289.

2. Indian Pharmacopoeia Volume III 2018,Page No:2899,2900.
REQUIREMENTS:

Furosemide, dimethyl formamide, sodium hydroxide, bromothymol blue indicator,0.1N oxalic acid,
Phenolphthalein indicator, conical flask, burette, beaker, funnel etc.

PRINCIPLE

It is assayed by aqueous acid base titration between weak acid furosemide and strong alkali sodium hydroxide. In
this assay protophilic solvent dimethyl formamide is used which enhances the acidity of furosemide so that it can
be titrated with sodium hydroxide. To make the effect of acid impurities present negligible a solvent blank
determination is carried out.

PREPARATION AND STANDARDIZATION OF STANDARD SOLUTIONS

a) SODIUM HYDROXIDE,XM
Solutions of any molarity xM may be prepared by dissolving 40x g of Sodium hydroxide in sufficient water to
produce 1000ml.

b) STANDARDIZATION OF 0.1M SODIUM HYDROXIDE SOLUTION

Weighed accurately about 5g of potassium hydrogen phthalate previously dried at 1200C for two hours dissolve
in 75ml of carbon dioxide free water. Added 0.1ml of phenolphthalein solution and titrate with the sodium
hydroxide until a permanent pink color is produced.

Each ml of 0.1M NaOH equivalent to 0.02042g of potassium hydrogen phthalate.

PROCEDURE:

a) ASSAY METHOD BY (NEUTRALIZATION TITRATION)

Weighed and powdered 20 tablets and Weighed accurately about a quantity of powder equivalent to 0.5g and
dissolve in 40ml of dimethyl formamide and titrate with 0.1M sodium hydroxide using bromothymol blue as an
indicator the end point shows the colour change from yellow to blue. Carry out a blank titration.

b) ASSAY METHOD BY (UV SPECTROPHOTOMETRY)

Weighed and powdered 20 tablets and Weigh accurately about a quantity of powder equivalent to 0.1g of
furosemide and shake with 150ml of 0.1M sodium hydroxide for 10 minutes. Added sufficient 0.1M sodium
hydroxide to produce 250ml and filter. Dilute 5ml to 200ml with 0.1M sodium hydroxide and measure the
absorbance of the resulting solution at the maximum at about [Link] the content of C12H11 ClN2O5S
taking 580 as the value of A (1%, 1cm) at the maximum at about 271 nm.

REPORT:

The given sample contains mg of furosemide.

 4. ASSAY OF IBUPROFEN

AIM:

To carry out the assay of Ibuprofen tablet

REFERENCE:

1. Indian Pharmacopoeia 2018 page no:2261-65.

REQUIREMENTS:

Ibuprofen,0.1N sodium hydroxide solution, phenolphthalein indicator, 0.1N oxalic acid solution, conical flask,
burette, beaker etc.

PRINCIPLE:

Ibuprofen is determined by neutralization titration in which free carboxylic group is titrated with sodium
hydroxide solution using phenolphthalein indicator. The amount of sodium hydroxide consumed in the reaction
indicates the amount of ibuprofen present in the sample.

PROCEDURE:

PREPARATION AND STANDARDIZATION OF STANDARD SOLUTIONS SODIUM HYDROXIDE,XM

Solutions of any molarity xM may be prepared by dissolving 40x g of Sodium hydroxide in sufficient water to
produce 1000ml.

STANDARDIZATION OF 0.1M SODIUM HYDROXIDE SOLUTION

Weighed accurately about 5g of potassium hydrogen phthalate previously dried at 1200C for two hours dissolve
in 75ml of carbon dioxide free water. Added 0.1ml of phenolphthalein solution and titrate with the sodium
hydroxide until a permanent pink color is produced.

Each ml of 0.1M NaOH equivalent to 0.02042g of potassium hydrogen phthalate. Phenolphthalein solution

A 1.0%w/v solution of phenolphthalein in ethanol(95%).

PROCEDURE:

Weighed and powdered 20 tablets. Weighed a quantity of powder containing about 0.4g of ibuprofen, dissolve in
100ml of ethanol (95%) and titrated with 0.1M sodium hydroxide using 0.2ml of phenolphthalein solution as
indicator. Perform a blank determination and make necessary correction.

Each ml of 0.1 M sodium hydroxide is equivalent to 0.02063 g of C13 H18 O2

REPORT

The given sample contains mg of Ibuprofen.

 5. ASSAY OF CHLORPROMAZINE

AIM:To carry out the Assay of Chlorpromazine. REFERENCE:Indian Pharmacopoeia 2018 page no:1600-01.
REQUIREMENTS:

Perchloric acid (0.1M),Chlorpromazine, mercuric acetate solution(5% w/v in acetic acid),crystal violet solution
(0.2%w/v in acetic acid),acetone,methyl orange indicator, conical flask, burette, beaker, potassium hydrogen
phthalate, glacial acetic acid, crystal violet indicator.

PRINCIPLE:

Chlorpromazine is estimated by non-aqueous titration which is suitable for titration of weak acid and weak base.
In this non aqueous solvent like perchloric acid is utilized as a titrant and methyl orange is used as an indicator.
Mercuric acetate is added in the non-aqueous titration in order to remove the chloride ions. So as to prevent the
interference of the chloride ion released by the titrant. The mercuric acetate replaces the halide ion in
chlorpromazine with acetate ion which is a strong base. The end point is indicated by appearance of blue colour.

PROCEDURE:

a) STANDARDISATION OF PERCHLORIC ACID (0.1N)

Dissolved 0.5g of potassium hydrogen phthalate in 25ml of glacial acetic acid and added few drops of 5%w/v
crystal violet indicator. Titrated the solution with 0.1N perchloric acid till blue green colour appears.

b) ASSAY OF CHLORPROMAZINE
Weighed accurately about 0.6g and dissolved in 200 ml of acetone. Added 15ml of mercuric acetate solution.
Titrated with 0.1M perchloric acid, using a saturated solution of methyl orange in acetone as indicator. Perform a
blank determination and make a necessary correction.

Each ml of 0.1M perchloric acid equivalent to 0.03553g of C17H19ClN2S,HCl

REPORT:

The given sample contains mg of chlorpromazine.

 6.

[Link] OF ATROPINE

AIM:

To carry out the assay of atropine.

REFERENCE:

1. Indian Pharmacopoeia 2018 page no:1600-01.

2. A textbook of Medicinal Chemistry-I,Pragi Arora,Varun Arora,Davinder Kumar,Page no:281,282

REQUIREMENTS:

Perchloric acid (0.1M),atropine,glacial acetic acid,crystal violet solution (0.2%w/v in acetic acid),acetone,methyl
orange indicator, conical flask, burette, beaker.

PRINCIPLE:

Atropine is assayed by non-aqueous titration which is generally used for the titration of weak acid with weak
base. In this titration non-aqueous solvent perchloric acid is used and crystal violet is used as an indicator. At the
end point blue colour is obtained.

PROCEDURE:

a) STANDARDISATION OF PERCHLORIC ACID (0.1N)

Dissolved 0.5g of potassium hydrogen phthalate in 25ml of glacial acetic acid and few drops of 5%w/v crystal
violet indicator. Titrated the solution with 0.1N perchloric acid till blue green colour appears.

b) ASSAY OF ATROPINE
Weighed accurately 400mg of atropine and dissolved it in 50ml of glacial acetic acid and added a drop of crystal
violet indicator. Titrated this solution with 0.1N perchloric acid until green color is obtained end point.
 [Link] OF
PARTITION COEFFICIENT
OF BENZOIC ACID
BETWEEN BENZENE
AND WATER
AIM:

To determine partition coefficient of benzoic acid between benzene and water.

REFERENCE:

1. Medicinal chemistry – I, Mrs Sheethal [Link], [Link] [Link], [Link] [Link], [Link],
[Link] page no:270-272.

2. Textbook of Practical chemistry 2008,K.S mukherjee, Page no:293.

REQUIREMENTS:

Separating funnel(250ml),conical flask ,pipette, burette, stoppered bottle, Saturated solution of benzoic acid in
benzene,benzene,0.01N NaOH, 0.1N NaOH and distilled water.

PRINCIPLE:

When a solute is shaken with two immiscible solvents it gets distributed between the solvents. This distribution
of solute in two solvents depends on the solubility of the solute in two solvents. At the distribution equilibrium,
the ratio of concentration of the solute in the two solvents is constant at a given temperature. The constant is
called partition coefficient (K) or the distribution coefficient of the solute between the two solvents.

PROCEDURE:

Prepared the following mixtures in separating funnels:

Set I: 25ml water + 25ml of saturated solution of benzoic acid in benzene.

Set II: 25ml water + 20 ml saturated solution of benzoic acid in benzene + 5ml benzene. Set III: 25ml water +
15ml saturated solution of benzoic acid in benzene + 10ml benzene.

Shaken the mixture in the separating funnel vigorously for about 30 minutes so that the benzoic acid gets
distributed between the two solvents and the distribution equilibrium is reached. Allowed the flasks to stand for
10 minutes to separate into two clear layers (removed the stopper of the separating funnel and keep its mouth
open during this period to facilitate the separation). Drain off the lower aqueous layers in 3 different stoppered
dry bottles. (Discard the intermediate layer between the two phases).Benzene layer remains in the separating
funnels. Using a dry pipette take 5ml of organic layer ( Benzene) into a conical flask containing 10ml of water and
titrate against 0.1N NaOH using Phenolphthalein as an indicator. The end point is indicated by the color change
from colorless to pink. Pipette out
10ml of the aqueous layer using dry pipette and titrate it against NaOH solution using phenolphthalein as an
indicator. End point is indicated by the color change from colorless to pink.

OBSERVATION

Set No. Vorg Vaq Norg = Corg Naq = Caq K logCorg log Caq

Mean partition coefficient (K) = Where,

Vorg = Volume in ml of 0.1N Sodium hydroxide per 5ml of organic layer Vaq = Volume in ml of 0.1N Sodium
hydroxide per 5ml of aqueous layer Norg = Normality of organic layer

Naq = Normality of aqueous layer

Corg = Concentration of organic layer in g mole/lit Caq = Concentration of aqueous layer in g mole/lit

K = Caq/ (Corg)1/2 = Partition coefficient of benzoic acid in water and benzene

CALCULATIONS

Set I:

For organic layer

Normality of NaOH (N1=0.1N)

Volume of Organic layer pipetted (V2) = 5ml N1V1 (Sodium hydroxide) = N2V2 (Organic layer)
N2 = 0.1 X V1 = Norg

Similarly calculate concentration of benzoic acid in organic layer of sets II and III

For aqueous layer

Normality of NaOH (N1=0.01N)

Volume of aqueous layer pipetted (V2) = 5ml N1V1 (Sodium hydroxide) = N2V2 (aqueous layer) N2 = 0.1 X V1
= Naq

Similarly calculate concentration of benzoic acid in aqueous layer of sets II and III

Graph

Plot the graph of logCaq Vs logCorg Partition coefficient (K) = Caq

Corg1/2 log Caq = 1/n log Corg + log K

Above equation is equation of a straight line (y = mx +c)

Result from graph Slope (m) =1/n Therefore n is nearly =

Substituting the value of slope of line in the equation log Caq = 1/n log Corg + log K

log Caq = log Corg + log K log K =

K=
REPORT:

1. Partition coefficient of benzoic acid between distilled water and benzene is………………….. by
calculation and by graph.

2. Since Caq/ Corg ½ is practically constant benzoic acid exists as a dimer (n=2) in benzene.
3. Molecular condition of benzoic acid in benzene is 1/slope = n
= ,molecules of benzoic acid associate in benzene.
[Link] OF PARTITION COEFFICIENT OF BENZOIC ACID BETWEEN BENZENE AND WATER

AIM:

To determine partition coefficient of benzoic acid between benzene and water.

REFERENCE:

1. Medicinal chemistry – I, Mrs Sheethal [Link], [Link] [Link], [Link] [Link], [Link],
[Link] page no:270-272.

2. Textbook of Practical chemistry 2008,K.S mukherjee, Page no:293.

REQUIREMENTS:

Separating funnel(250ml),conical flask ,pipette, burette, stoppered bottle, Saturated solution of benzoic acid in
benzene,benzene,0.01N NaOH, 0.1N NaOH and distilled water.

PRINCIPLE:

When a solute is shaken with two immiscible solvents it gets distributed between the solvents. This distribution
of solute in two solvents depends on the solubility of the solute in two solvents. At the distribution equilibrium,
the ratio of concentration of the solute in the two solvents is constant at a given temperature. The constant is
called partition coefficient (K) or the distribution coefficient of the solute between the two solvents.

PROCEDURE:

Prepared the following mixtures in separating funnels:

Bottle no: Volume of ether Volume of Water Volume of Benzoic acid

1 20ml 20ml 0.25g

2 20ml 20ml 0.5g

a) Standardization of 0.1M Sodium hydroxide

Dissolved 0.5g of potassium hydrogen phthalate in 75ml of water and added 0.1ml phenolphthalein as indicator
and titrated using 0.1M NaOH.

Each ml of 0.1M Sodium hydroxide= 0.02042g of Potassium hydrogen phthalate.

 b) Determination of Partition Coefficient
The bottles are well stoppered and shaken for [Link] completion of shaking the mixture is allowed to
stand 20-30 minutes. So that the two layer separate completely ether is lighter than water and exist at top while
water remains at lower portion. Ether layer is evaporated to dryness and residue was dissolved in 10ml ethanol
and titrates with 0.1M NaOH using phenolphthalein as indicator. Similarly 10ml of water is pipetted out and
titrate with 0.1N NaOH.

Each ml of 0.1M NaOH = 0.01221g of benzoic acid.

REPORT :

The log P value of benzoic acid in bottle 1 = The log P value of benzoic acid in bottle 2 =

.
CALCULATIONS

Standarisation of Sodium hydroxide

[Link] Contents Burette reading Volume of NaOH (ml) Indicator Endpoint

of
conical flask Initial Final

Molarity of NaOH = Weight taken X Expected Molarity

Titre value X [Link] Factor

Bottle 1(0.25g of benzoic acid)

[Link] Contents Burette reading Volume of NaOH (ml) Indicator Endpoint

of Bottle
1 Initial Final

1 Residue + 10ml
ethanol (ether
layer)

2 10mlwater layer
+10ml ethanol

(water layer)

Bottle 2(0.5g of benzoic acid)

[Link] Contents Burette reading Volume of NaOH (ml) Indicator Endpoint

of Bottle
1 Initial Final
 1 Residue + 10ml
ethanol (ether
layer)

2 10mlwater layer
+10ml ethanol

(water layer)

Bottle 1(0.25g of benzoic acid)

Concentration of benzoic acid in aqueous layer =

titre value X actual normality X [Link]

factor

Expected normalityX Vol:pipetted

Concentration of benzoic acid in organic layer = titre value X actual normality X [Link] factor

Expected normality X Vol:pipetted

Bottle 2(0.5g of benzoic acid)

Concentration of benzoic acid in aqueous layer =

titre value X actual normality X [Link]

factor

Expected normality X Vol:pipetted

Concentration of benzoic acid in organic layer = titre value X actual normality X [Link] factor

Expected normality X Vol:pipetted

Partition coefficient of benzoic acid in bottle 2 = titre value X actual normality X [Link] factor

Expected normalityX Vol:pipetted

[Link] OF BENZIMIDAZOLE

AIM: To prepare and submit benzimidazole from o-phenylenediamine.

REFERENCE:

1. Medicinal chemistry – I, Mrs Sheethal [Link], [Link] [Link], [Link] [Link], [Link], [Link]
page no:233-235.

REQUIREMENTS:

Round bottom flask, Beaker, Measuring cylinder,Waterbath, Buchner funnel, O-phenylene diamine, Formic
acid(90%),Sodium hydroxide (10%)

PRINCIPLE:

The preparation of benzimidazole can be done by reaction between O-phenylene diamine with formic acid in
presence of base i.e sodium [Link] is a condensation type of reaction in which o-phenylene diamine
condensed with formic acid to give benzimidazole with removal of two molecules of water.

NH2 N

HCOOH

NaOH

NH2 NH

O-phenylene diamine Benzimidazole

PROCEDURE:

Placed 27g of O-phenylenediamine in a round bottomed flask of 250ml and added 17.5g (16ml) of 90% formic
acid. Heated the mixture on a water bath at 1000C for 2 hour. Cooled and added 10% sodium hydroxide solution
slowly, with constant rotation of the flask, until the mixture is just alkaline to litmus. Filter off the synthesized
crude benzimidazole by using the pump wash with ice cold water.

Recyrstallisation: Dissolved the synthesized product in 400ml of boiling water, added 2g of decolorizing carbon
and digest for 15minutes. Filter rapidly through Buchner funnel and a flask at the pump. Cool the filtrate to
about 100C, filter off the benzimidazole, wash with 25ml of cold water and dry at 1000C. The yield of pure
benzimidazole is 25g (85%), m.p 171- 1720C.
CALCULATION

Here limiting reagent is O-phenylene diamine; hence yield should be calculated from its amount taken.

Molecular formula of O-phenylene diamine = C6H8N2 Molecular formula of benzimidazole = C7H6N2 Molecular
weight of O-phenylene diamine = 108g/mole Molecular weight of benzilidazole = 118g/mole

108g of O-phenylene diamine forms 118g benzimidazole

Therefore, 27g O-phenylene diamine will form………(X) g benzimidazole X = (118 X 27)/108 = 29.5g

Theoretical yield = 29.5g Practical yield = g

% yield = (practical yield) X 100

(theoretical yield)

REPORT:

Benzimidazole was synthesized from O-phenylene diamine and submitted.

10. SYNTHESIS OF BENZOTRIAZOLE

AIM:

To synthesize and submit benzotriazole from o-phenylene diamine and report its percentage yield.

REFERENCE:

1. Practical medicinal chemistry by Dr. Devala Rao, page no:35.

2. Comprehensive practical organic chemistry by [Link] and Renu Aggarval, page no:121.
CHEMICAL REQUIREMENTS:

o-phenylenediamine, glacial acetic acid, sodium nitrite

PRINCIPLE:

The sodium nitrite reacts with glacial acetic acid and liberates nitrous acid. The o-phenylene diamine reacts with
nitrous acid and produce diazonium ion. When the structure and stereochemistry of diazonium ion are stable,
intramolecular nitrogen coupling occurs and form benzotriazole directly.

NaNO2 + CH3COOH HNO2 + CH3COONa

sodiu m sodium acetate

nitrite
nitrou acid

NH2 + - H+ N

N N N

H+

NH2 NH

- 2H2O NH2

o-phenylene D benzotriazole
diamine
CALCULATIONS

Molecular weight of o-phenylene diamine = Molecular weight of benzotriazole =

---- g of o-phenylene diamine gives g of benzotriazole

1g of o-phenylene diamine =

---- g of o-phenylene diamine =

Theoretical yield =

Practical yield =

𝑃𝑟 x 100
𝑎𝑐𝑡
Percentage yield

𝑖𝑐𝑎
=

𝑙
𝑦𝑖𝑒
𝑙𝑑
PROCEDURE:

𝑡ℎ𝑒
𝑜𝑟
𝑒𝑡𝑖
𝑐𝑎𝑙
𝑦𝑖𝑒
𝑙𝑑

Dissolve 1.3g of o-phenylenediamine in a mixture of 1.5ml of glacial acetic acid and 5ml water in a beaker. Stir
until the solid dissolves, warm gently if necessary. Cool the solution to 150C. Stir well and add a solution of 2g of
sodium nitrite in 2ml water. Reaction mixture become warm within 2-3 minutes and reaches a temperature of
about 850C and then begins to cool. Colour changes from deep red to pale brown. Continue stirring for 15
minutes till the temperature fall about 35-400C. Thoroughly chill in ice bath for 30 minutes. Filter the product and
wash with cold water.

USE:

Used in bulk drug industry as an important intermediate compound.

It is the basic nucleus present in anthelmintic drugs like mebendazole, thiabendazole etc.

REPORT:
Benzotriazole was prepared and submitted. The percentage yield was found to be ---------
11. SYNTHESIS OF 2,3-DIPHENYL QUINOXALINE

AIM:

To synthesize and submit 2,3-diphenyl quinoxaline from o-phenylenediamine and report its percentage yield.

REFERENCE:

1) Vogels textbook of practical organic chemistry,5th edition, page no:90.

2) Comprehensive practical organic chemistry by [Link] and Renu Aggarwal, page no:123.
CHEMICAL REQUIREMENTS:

o-phenylenediamine, benzil, rectified spirit.

PRINCIPLE:

Quinoxalines are a type of heterocyclic compounds. They are also known as benzopyrazines.

N N

N N

benzopyrazine pyrazine

Generally quinoxaline is formed by the condensation of o-phenylenediamine with diketones. Here 2,3-diphenyl
quinoxaline is prepared by treating o-phenylenediamine with benzil.

NH2 N CH

O C C6H5 65

NH O C C6H5 CH

2 N 65

o-phenylene diamine benzil 2,3,-diphenyl quinoxaline

CALCULATIONS

Molecular weight of 2, 3-diphenyl quinoxaline = Molecular weight of o-phenylene diamine =

----- g of o-phenylene diamine gives g of 2, 3-diphenyl quinoxaline

1g of o-phenylene diamine =

----- g of o-phenylene diamine =

Theoretical yield =

Practical yield =

𝑃𝑟 x 100
𝑎𝑐𝑡
Percentage yield

𝑖𝑐𝑎
=

𝑙
𝑦𝑖𝑒
𝑙𝑑

𝑡ℎ𝑒
𝑜𝑟
𝑒𝑡𝑖
𝑐𝑎𝑙
𝑦𝑖𝑒
𝑙𝑑

PROCEDURE:

Add a solution of 1.1g of o-phenylenediamine in 8ml rectified spirit to a warm solution of

2.1 g of benzil in 8ml rectified spirit. Warm the mixture for 30 minutes in a water bath. Add water dropwise until
slight cloudiness persists. Cool the solution and filter the product.

USE:
Quinoxaline derivatives are used as antimicrobial agents like levomycin. They are also used in dyes.

REPORT:

2,3-diphenyl quinoxaline was prepared and submitted. The percentage yield was found to be ---------
12. SYNTHESIS OF PHENYTOIN AIM:

To prepare and submit recrystallized dried product of phenytoin and calculate

(i) Percentage yield

(ii) Melting point

REFERENCE:

Medicinal chemistry theory and practical by and practical by Prof:[Link],[Link]

Muzumder,[Link] page no:9

REQUIREMENTS:

Chemicals used: Urea, Nitric acid, Benzoin, Sodium hydroxide, ethanol, conc:HCl Apparatus used: Round bottom
flask ,reflex condenser, funnel, beaker, filter paper, glass rod.

PRINCIPLE:

Phenytoin is 5,5-diphenyl imidazoline 2,[Link] react with urea in the presence of alkali and alcohol to
give phenytoin by pinacolone rearrangement.
PROCEDURE:

a) Preparation of Benzil from Benzoin:

Place 2g of benzoin and 5ml of concentrated HNO3 in a round bottom flask and heat on a boiling water bath till
crystalline benzoin is replaced by oily [Link] the mixture in to beaker of cold water with stirring the oily
benzil crystallize in to yellow salt.

b) Preparation of phenytoin from benzil:

Place 1g benzil, 1g urea ,5ml 30% aqueous sodium hydroxide and 20ml ethanol in a round bottom flask which is
attached to reflux condenser and boil for [Link] the mixture to attain room [Link] the mixture
to 100ml water and,mix and allow to stand for [Link] to remove insoluble [Link] the
filtrate strongly acidic with concentrated HCl .Cool the filtrate in ice cold [Link] the precipitate product dry
and submit.

IDENTIFICATION

Experiment Observation Inference

To the sample solution add White precipitate Presence of phenytoin

hydrochloric acid

To the sample add pyridine and Blue colour Presence of phenytoin

copper sulphate

solution

REPORT:-
13. SYNTHESIS OF BENZOCAINE [ETHYL PARA AMINO BENZOATE]

AIM:

To synthesis recrystallized product of benzocaine from para amino benzoic acid and calculate

(i) Percentage yield

(ii) Melting point

REFERENCE:

Medicinal chemistry theory and practical by and practical by Prof:[Link],[Link]

Muzumder,[Link] page no:22

REQUIREMENTS:

PABA, Conc:sulphuric acid, ethanol,reflux condenser, RB flask , beaker

PRINCIPLE:

Benzocaine is the ethyl ester of para amino benzoic acid(PABA).It can be prepaired from PABA and ethanol by
fischer esterification.

COOH COOCH 2CH3

+ CH3CH2OH

NH2 NH2

PABA Ethy para amino benzoate

PROCEDURE:

To a 100ml RB flask, add 8ml of ethanol, 4.12g of para amino benzoic acid(PABA) and 1.2ml of conc:H2SO4 keep
the mixture under reflux for 1hour up on cooling reaction mixture sets to a solid mass of hydrochloride of ethyl
para amino benzoate. Pour the hot solution in to excess of water(no hydrochloride) add Na2CO3 to the clear
solution until it is neutral to litmus. Filter wash and dry the product.

IDENTIFICATION

EXPERIMENT OBSERVATION INFERENCE

To the sample solution add Deep red colour Benzocaine confirmed

sodium nitrite and [Link] and
cool the mixture. To this add a
solution of beta naphthol in
sodium hydroxide. Maintain the
temperature at 0 to 5°

REPORT:-