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The Hofmann Reaction

  1. Everett S. Wallis,
  2. John F. Lane

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or003.07

Organic Reactions

Organic Reactions

How to Cite

Wallis, E. S. and Lane, J. F. 2011. The Hofmann Reaction . Organic Reactions. 3:7:267–306.

Author Information

  1. Princeton University

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

In the Hofmann reaction an amide is converted to an amine of one less carbon atom by treatment with bromine or chlorine, and alkali. In effect, the carbonyl group of the amide is eliminated. The reaction is applicable to the preparation of amines from amides of aliphatic, aromatic, arylaliphatic, and hetereocyclic acids. The Hofmann reaction is generally carried out by dissolving the amide in a very slight excess of cold aqueous hypohalite solution, followed by rapid warming, A valuable modification consists in carrying out the reaction in an alcoholic solution, with subsequent hydrolysis of the urethan so obtained.

Keywords:

  • Hofmann reaction;
  • amides;
  • side reactions;
  • alkaline sodium hypobromite;
  • alkaline sodium hypochlorite;
  • experimental conditions