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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 11, pp 1204–1208 | Cite as

3-Indolylphenylacetonitriles

  • N. A. Kogan
Article
  • 26 Downloads

Abstract

The reaction of 2-carbethoxyindole with aromatic aldehydes in ether saturated with HCl gave 2-carbethoxy-3-(α-chlorobenzyl)indoles. Reaction of the latter with sodium cyanide in dimethyl sulfoxide gave 3-indolylphenylacetonitriles in 47–85% yields. If the indole NH group is substituted, rearrangment to give 1-methyl-2-cyano-3-benzylindoles occurs simultaneously. The latter were reduced with LiAlH4 to aminomethyl derivatives and were hydrolyzed with KOH in ethylene glycol to 1-methyl-3-benzylindole-2-carboxylic acids. The structures were proved by the UV, IR, and PMR spectra.

Keywords

Sodium Ether Organic Chemistry Ethylene Glycol Aldehyde 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1979

Authors and Affiliations

  • N. A. Kogan
    • 1
  1. 1.Leningrad Pharmaceutical-Chemistry InstituteLeningrad

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