Benzeneacetonitrile, 2,3-dichloro- → Ammonia

Participants

Reaction Steps

A solution of 2,3-dichlorophenylacetonitrile (0.5 g, 2.7 mmol) in diethyl ether (5 mL) was added to an ice-cold solution of lithium aluminium hydride (1M in diethyl ether, 2.7 mL, 2.7 mmol) and aluminium trichloride (359 mg, 2.7 mmol). The mixture was stirred at room temperature 2.5 hours and was then quenched with 1M sodium hydroxide solution (5 mL). The mixture was stirred for a further 30 minutes and filtered through Celite®. The layers of the filtrate were separated and the organic solution was concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 95:5:0.5 afforded the title compound as a clear oil in 26% yield, 135 mg. 1H NMR (400 MHz, CDCl3) δ 7.38 (1H, dd), 7.27-7.19 (2H, m), 2.95 (2H, m), 2.87 (2H, m) ppm; LRMS APCI m/z 190 [M+H]+

Provenance & Evidence