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Knoevenagel Diazotization Method

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr362

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Knoevenagel Diazotization Method. Comprehensive Organic Name Reactions and Reagents. 362:1627–1630.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of an anhydrous diazonium salt by the treatment of primary amine with amyl nitrite in an acidified absolute alcohol, by which a crystalline precipitate of the diazonium salt is formed on standing or on the addition of a small quantity of ether is generally known as Knoevenagel diazotization method. It has been found that under these conditions nitrous acid is generated in situ, which then diazotizes the amines. The study finds that the reaction of aromatic amine with amyl nitrite in aromatic solvents affords a moderate yield of biaryls, which indicate the presence of aryl radicals. This reaction is useful for the synthesis of anhydrous diazonium salts.

Keywords:

  • diazonium salt;
  • diazohydroxide;
  • nitrous acid;
  • m-nitrobenzenediazonium