Aluminium lithium hydride → N-methyl(3-vinyl-1H-indol-2-yl)methanamine

Participants

Reaction Steps

A solution of N-methyl-3-vinyl-1H-indole-2-carboxamide (740 mg, 3.7 mmol) in dioxane was added slowly to an ice-cooled solution of lithium aluminium hydride (2.1 g, 55.5 mmol) in dioxane (100 mL). The mixture was stirred at reflux overnight. Excess lithium aluminium hydride was quenched with 15% NaOH (10 mL) and the mixture separated. The aqueous phase was washed twice with ethyl acetate and the combined organic phases dried to afford the title compound (430 mg 61%). 1H NMR (400 MHz, DMSO-d6) δ 11.09 (s, 1H), 7.75 (d, J=8 Hz, 1H), 7.49 (d, J=6.4 Hz, 1H), 7.09-7.05 (m, 2H), 7.04-6.90 (m, 1H), 5.54 (d, J=16 Hz, 1H), 5.06 (d, J=10.0 Hz, 1H), 3.84 (s, 2H), 2.27 (s, 3H).

Provenance & Evidence