Water → (1H-indol-5-yl)methanamine

Participants

Reaction Steps

A solution of 1H-indole-5-carbonitrile (3.7 g) in tetrahydrofuran (25 ml) was added over fifteen minutes to a stirred suspension of lithium aluminium hydride (3.1 g) in tetrahydrofuran (80 ml) under nitrogen. After thirty minutes, the suspension was heated at reflux for two hours. After cooling to 0°, water (3.1 ml), sodium hydroxide (2N, 6.2 ml) and water (9.3 ml) were added with caution, the resulting salts were filtered off and the filtrate was concentrated under vacuum to afford a yellow oil (3.3 g) which was crystallised from ethyl acetate to give the title compound as a pale cream solid m.p. 114°-5°.

Provenance & Evidence