An approach to expound Aniline.

1. REACTIONS AND
PHARMACEUTICAL
APPLICATIONS OF ANILINE
BY: MASH’HOOD MAHMOOD KHAN
SHAHID

2. ANILINE
o A benzene derivative in which one Hydrogen atom is
substituted with an amino group.
o Also known as Phenylamine or Aminobenzene.
o It’s a prototypical aromatic amine.

3. CHEMICAL NATURE
 Reaction due to NH2
group
 Reaction due to C6H5
group

4. REACTIONS INVOLVING –NH2
GROUP
Following is the list of reactions of aniline involving amino group:
o Salt Formation
o Alkylation
o Acylation
o Reaction with Acetaldehyde
o Carbylamine Reaction

5. REACTIONS DUE TO BENZENE
RING
Following is the list of reactions of aniline involving amino group:
o Oxidation
o Hofmann Martius Rearrangement
o Halogenation
o Sulphonation
o Nitration

7. SALT FORMATION
NH2 NH3Cl
HCl
Aniline form salt when reacted with mineral acids
such as HCl and H2SO4.

8. ALKYLATION
NH2 CH3-
NH2Cl
NHCH3
NHCH3
CH3Cl HCl
-HCl
+ –
NaOH
• Aniline react with alkyl halide to form 2º and 3º amines.
• The amines so formed react with HX to form salts.
• These salts can be treated with aq. NaOH to give free 2º
and 3º amines. + –

9. ALKYLATION
CH3-NH-ClCH3-N-CH3
CH3-N-
CH3
CH3Cl HCl
-HCl
+ –
NaOH
NHCH3
CH3
Alkylation of 2º amines;

10. ACYLATION
NH2
CH3–C–
Cl
O
CH3–C–O –C –CH3
O O
NH–C –
CH3
NH–C–CH3
O
O
–HCl
–CH3COOH
With acid halides and anhydrides, they
form N-aryl amides.

11. REACTION WITH
ACETALDEHYDE
NH2 N=CH-
CH3
CH3–C–
H
O
– H2O
Aniline on reaction with acetaldehyde results in imine
(Schiff’s base).

12. CARBYLAMINE REACTION
NH2
CH3
Cl
3KOH&
–
3KCl
& –
3H2O
NC
Aniline react with chloroform and alcoholic potash to
form phenyl isocyanide, the reaction is Carbylamine
Reaction.

14. Electron donating effect of –NH2
group to benzene ring.

15. OXIDATION
NH2 O
O
K2Cr2O7 / H+
[O]
Aromatic amines are readily oxidized to give products
depending upon conditions.
Para
benzoquinone

16. HOFMANN MARTIUS
REARRANGEMENT
CH3-N.HCl
CH3
400º
C
CH3-N.HCl
H
CH3
-
N.HCl
H
CH3
H-N-H
CH3
NaOH
CH3
CH3
With N-N- dialkyleaniline in strong acid media at 400ºC,
intermolecular migration occurs.
H
2,4- dimethyl
aniline

17. HALOGENATION
NH2 NH2
3Br
2
H
H
H
Aniline reacts with Br2 readily even below 5ºC to form
white ppt. of o,p-tribromoaniline.
-
3HBr
Br
Br
Br
o,p-
tribromoaniline

18. SULPHONATION
NH2 NH2
SO3H
H2SO
4
180ºC&
– H2O
On heating with fuming sulfuric acid, aniline is
sulfonated to form sulfanilic acid.
sulfanilic acid.

19. NITRATION
NH2
HNO
3
NH3ONO2 H-N-H
NaOH
H2SO
4
HNO
3
H2SO
4
+ -
NH3ONO2
+ -
NO
2
NO
2
On treatment with conc. HNO3 and conc. H2SO4 in the
presence of acetic anhydride, aniline undergoes nitration
to give m-nitro aniline.
m-nitro
aniline

20. Diazotization
 Much like in primary aliphatic amines, amino benzene
(aniline) is converted into a diazonium ion by treating
it with a nitrous acid and mineral acid mixture.
Formally, a nitrosyl cation (NO+) is then transferred to
the amine.

21. Wohl–Aue Reaction
 The Wohl-Aue Reaction is an organic reaction
between an aromatic nitro group and aniline to form a
phenazine in the presence of alkali base.

22. POLYMERIZATION
Oxidation with persulfate affords a variety
of polyanilines compounds. These polymers exhibit rich redox
and acid-base properties.

24. PHARMACEUTICAL
APPLICATION
Aniline has wide range of pharmaceutical products
magnanimously used for the welfare of mankind.
Here are the examples of few of them;
 Acetanilide
 3- Trifluoromethylaniline
 Sulfa Drugs

25. Acetanilide
 A key intermediate for the manufacture of sulfa
drugs.
 Precursor in the synthesis of Penicillin.

26. PARACETAMOL
Also it is known as acetaminophen.
It is used as antipyretic.

27. 3-trifluromethylaniline
o Intermediate for herbicides,
fungicides
and metabolites.

28. SULPHONAMIDE MEDICINE
Aniline derivatives of sulphonamide
are Anti-microbial drug with short
action period.
Sulfafurazol Sulfadiazi
ne
Sulfacetami
de
Sulfisomidin
e

29. SULFAPYRIDINE:
 Used to treat linear IgA
dermatosis.
 Good antibacterial drug.
SULFACETAMIDE:
 Use in the treatment of pityriasis
versicolor.
 Anti-inflammatory in conjunctivitis.
SULFANILAMIDE:
 For treating certain vaginal infections.
 Block the growth activity of certain
bacteria.
SUCCINYLSULFATHIAZOLE:
 Ultra long acting drug.
 Used for antibacterial activity in GIT.

30. THE END
REVOLUTIONARY PATHAN
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