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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.
KeywordsSodium Ether Organic Chemistry Ethylene Glycol Aldehyde
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