schmidt reaction

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Schmidt Reaction:

In presence of concentrated H2SO4,carboxylic acid react with hydrazoic acid, to give amine.

amine

when aldehyde reacts with hydrazolic acid then a mixture of cyanide and formyl derivatives are formed.

aldehyde

when ketone reacts with hydrazoic acid then amides are formed.

amides

Mechanism:

a) Reaction with carboxylic acid.

carboxylic1

carboxylic2

 

carboxylic3

 

carboxylic3jpg

 

 

carboxylic5

 

b)Reaction with aldehyde:

aldehyde1

 

 

aldehyde2

 

aldehyde3

aldehyde4

 

c)Reaction with ketone:

ketone12

ketone34

ketone56

Applications:

1)Preparation of primary amines-

This reaction is useful in the direct conversion of carboxylic acid into primary amine but hydrazoic acid is explosive and poisonous in nature.

2)Preparation of  -amino acid-

Another use of Schmidt reaction is to synthesize -amino acid from aceto acetic ester.