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Replacement of the Aromatic Primary Amino Group by Hydrogen

  1. Nathan Kornblum

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or002.07

Organic Reactions

Organic Reactions

How to Cite

Kornblum, N. 2011. Replacement of the Aromatic Primary Amino Group by Hydrogen . Organic Reactions. 2:7:262–340.

Author Information

  1. Harvard University, Oberlin College

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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Abstract

The replacement of an aromatic primary amino group by hydrogen is usually effected by the reduction of the diazonium salt derived from the amine. It is evident that the success of the deamination process is a function of the completeness of diazotization as well as of the reduction. Diazonium compounds have been treated with a great variety of reducing agents some of which have become incorporated into procedures for replacing the diazo group by hydrogen. The important process involve reduction by: alcohols, hypophosphorous acid, alkaline formaldehyde, stabilization of the diazonium salt with naphthalene-1,5-disulfonic acid followed by treatment with zinc or copper, sodium stannite, stannous chloride or sodium sulfate reduction to hydrazine from which the hydrocarbon is obtained by oxidation.

Keywords:

  • replacement;
  • primary amino group;
  • hydrogen;
  • alcohols;
  • hypophosphorous acid;
  • alkaline formaldehyde;
  • stabilization;
  • diazonium salt;
  • naphthalene-1,5-disulfonic acid;
  • sodium stannite;
  • stannous chloride;
  • sodium sulfate reduction;
  • hydrazine