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REACTIONS AND PHARMACEUTICAL APPLICATIONS OF ANILINEBY: MASHHOOD
MAHMOOD KHAN SHAHID
ANILINEA benzene derivative in which one Hydrogen atom is
substituted with an amino group.Also known as Phenylamine or
Aminobenzene.Its a prototypical aromatic amine.
CHEMICAL NATUREReaction due to NH2 groupReaction due to C6H5
group
REACTIONS INVOLVING NH2 GROUP Following is the list of reactions
of aniline involving amino group:Salt
FormationAlkylationAcylationReaction with AcetaldehydeCarbylamine
Reaction
REACTIONS DUE TO BENZENE RINGFollowing is the list of reactions
of aniline involving amino group:
OxidationHofmann Martius
RearrangementHalogenationSulphonationNitration
RAECTIONS DUE TO AMINO GROUP
SALT FORMATION
NH2NH3ClHClAniline form salt when reacted with mineral acids
such as HCl and H2SO4.
ALKYLATION
NH2
CH3-NH2Cl
NHCH3
NHCH3CH3ClHCl-HCl
+ NaOHAniline react with alkyl halide to form 2 and 3 amines.
The amines so formed react with HX to form salts.These salts can be
treated with aq. NaOH to give free 2 and 3 amines.+
ALKYLATION
CH3-NH-Cl
CH3-N-CH3
CH3-N-CH3CH3ClHCl-HCl
+ NaOH
NHCH3CH3Alkylation of 2 amines;
ACYLATION
NH2CH3CClOCH3CO C CH3OO
NHC CH3
NHCCH3OOHClCH3COOHWith acid halides and anhydrides, they form
N-aryl amides.
REACTION WITH ACETALDEHYDE
NH2
N=CH-CH3CH3CHO H2OAniline on reaction with acetaldehyde results
in imine (Schiffs base).
CARBYLAMINE REACTION
NH2CH3Cl3KOH& 3KCl& 3H2O
NCAniline react with chloroform and alcoholic potash to form
phenyl isocyanide, the reaction is Carbylamine Reaction.
REACTIONS DUR TO BENZENE RING..
Electron donating effect of NH2 group to benzene ring.
OXIDATION
NH2
OOK2Cr2O7 / H+[O]Aromatic amines are readily oxidized to give
products depending upon conditions.Para benzoquinone
HOFMANN MARTIUS REARRANGEMENT
CH3-N.HClCH3400C
CH3-N.HClHCH3
-N.HClHCH3
H-N-HCH3NaOHCH3CH3With N-N- dialkyleaniline in strong acid media
at 400C, intermolecular migration occurs.H2,4- dimethyl aniline
HALOGENATION
NH2
NH23Br2 HHHAniline reacts with Br2 readily even below 5C to form
white ppt. of
o,p-tribromoaniline.-3HBrBrBrBro,p-tribromoaniline
SULPHONATION
NH2
NH2SO3HH2SO4 180C
& H2OOn heating with fuming sulfuric acid, aniline is
sulfonated to form sulfanilic acid.sulfanilic acid.
NITRATION
NH2HNO3
NH3ONO2
H-N-HNaOHH2SO4 HNO3H2SO4 +-NH3ONO2+-NO2NO2On treatment with
conc. HNO3 and conc. H2SO4 in the presence of acetic anhydride,
aniline undergoes nitration to give m-nitro aniline.m-nitro
aniline
DiazotizationMuch like in primary aliphaticamines, 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.
WohlAue ReactionThe Wohl-Aue Reaction is an organic reaction
between an aromatic nitro group and aniline to form a phenazine in
the presence of alkali base.
POLYMERIZATION
Oxidation with persulfate affords a variety
ofpolyanilinescompounds. These polymers exhibit rich redox and
acid-base properties.
PHARMACEUTICAL APPLICATIONS
PHARMACEUTICAL APPLICATIONAniline has wide range of
pharmaceutical products magnanimously used for the welfare of
mankind. Here are the examples of few of them;Acetanilide3-
Trifluoromethylaniline Sulfa Drugs
AcetanilideA key intermediate for the manufacture of sulfa
drugs. Precursor in the synthesis of Penicillin.
PARACETAMOL
Also it is known as acetaminophen.It is used as antipyretic.
3-trifluromethylaniline
Intermediate for herbicides, fungicides and metabolites.
SULPHONAMIDE MEDICINE
Aniline derivatives of sulphonamide are Anti-microbial drug with
short action
period.SulfafurazolSulfadiazineSulfacetamideSulfisomidine
SULFAPYRIDINE:Used to treat linear IgA dermatosis.Good
antibacterial drug.SULFACETAMIDE:Use in the treatment ofpityriasis
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.
Linear IgA dermatosis is a rare immune-mediated blistering skin
disease. Pityriasis versicolor skin eruption on the trunk and
proximal extremities.Conjunctivitis, also known aspink
eye[1]orMadras eye[2]isinflammationof theconjunctiva(the outermost
layer of theeyeand the inner surface of theeyelids)29
THE END
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