THE HYDROGENOLYSIS OF 3-HYDROXYMETHYLINDOLE AND OTHER INDOLE DERIVATIVES WITH LITHIUM ALUMINUM HYDRIDE
- 1 September 1953
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 31 (9) , 775-784
- https://doi.org/10.1139/v53-106
Abstract
Indole-3-aldehyde, indole-3-carboxylic acid and its ethyl ester were reduced by excess lithium aluminum hydride to skatole. The expected reduction product, 3-hydroxymethylindole, was obtained by the action of sodium hydroxide on gramine methiodide. It and its alkyl ethers were readily reduced to skatole. 3-Hydroxymethylindole underwent self-condensation to 3,3′-di-indolylmethane in neutral and alkaline media, and with acidic reagents was converted to an oxygen-free polymeric substance. The mechanism of these reactions and of the hydrogenolysis is discussedKeywords
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