General methods of preparation
(i) Methods yielding mixture of amines (Primary, secondary and tertiary)
(a) Hofmann's method :The mixture of amines (1°, 2° and 3°) is formed by the alkylation of ammonia with alkyl halides.
The primary amine can be prepared in a good yield by using a large excess of ammonia. The process is also termed as ammonolysis of alkyl halides. It is a nucleophilic substitution reaction.
(b) Ammonolysis of alcohols :
Primary amine may be obtained in a good yield by using a excess of ammonia.
(ii) Methods yielding primary amines
(a) Reduction of nitro compounds
(b) Reduction of nitriles (Mendius reaction)
The start can be made from alcohol or alkyl halide.
This sequence gives an amine containing one more carbon atom than alcohol.
(c) By reduction of amides with LiAlH4
(d) By reduction of oximes : The start can be made from an aldehyde or ketone.
(e) Hofmann's bromamide reaction or degradation (Laboratory method) : By this method the amide (-CONH2) group is converted into primary amino (- NH2) group.
This is the most convenient process for creating primary amines.
This method provides an amine containing one carbon atom less than amide.
(f) Gabriel phthalimide synthesis : This method involves the following three steps.
· Phthalimide is reacted with KOH to form potassium phthalimide.
· The potassium salt is treated with an alkyl halide.
· The product N-alkyl phthalimide is put to hydrolysis with hydrochloric acid when primary amine is formed.
When hydrolysis is difficult, the N-alkyl phthalimide can be treated with hydrazine to give the required amine.
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