Reissert Indole Synthesis
Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Reissert Indole Synthesis. Comprehensive Organic Name Reactions and Reagents. 528:2341–2344.
- Published Online: 15 SEP 2010
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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.
- o-nitrophenylpyruvic ester;
- copper chromite