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Reissert Indole Synthesis

(Reissert Condensation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr528

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Reissert Indole Synthesis. Comprehensive Organic Name Reactions and Reagents. 528:2341–2344.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The multistep synthesis of indole derivatives from ortho-nitrotoluene involving the basic condensation of o-nitrotoluene with oxalic ester to o-nitrophenylpyruvic ester, reduction of the nitro group to an amino group, cyclization to indole-2-carboxylic acid and final decarboxylation is generally referred to as the the Reissert indole synthesis. All the mechanistic features of the reaction have been discussed. It has been found that the hydrogenation of 2-nitrophenylpyruvate ester with 5% Pd/C in EtOH is the best reduction condition for this reaction. This reaction has been modified by reduction of o-nitrophenylpyruvic ester with stannous chloride dihydrate in DME at ambient temperature. This reaction has been applied in the preparation of indole derivatives.

Keywords:

  • o-nitrophenylpyruvic ester;
  • o-nitrotoluene;
  • 1,2,3,4-tetrahydro-2-quinolone;
  • copper chromite