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Reaction of l-methyl-2-cyanoindole with aromatic aldehydes

Research paper by N. A. Kogan

Indexed on: 01 Jun '76Published on: 01 Jun '76Published in: Chemistry of Heterocyclic Compounds



Abstract

1-Methyl-2-cyanoindoles react with aromatic aldehydes in acidic media to give 1-methyl-2-cyano-3-(α-halobenzyl)indoles. Replacement of the halogen by a cyano group gives (indolyl)-phenylacetonttrile, reduction of which gives the corresponding tryptamine. An attempt to replace the acetoxy group in 1-methyl-2-carbomethoxy-3-(α-acetoxybenzyl)indole by a cyano group was accompanied by rearrangement to give 1-methyl-2-cyano-3-benzylindole.