Hydrochloric Acid → 1-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,2,3,4-Tetrahydro-benzo[b]azepin-5-one (500 mg, 3.1 mmol) in pyridine (2 ml) is added p-toluenesulfonyl chloride (650 mg, 3.4 mmol), and the mixture is heated at 50° C. for 1 hour. The reaction mixture is poured into 1N HCl (100 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated to a solid. The solid is purified by silica gel column chromatography (eluent, 30% ethyl acetate in hexanes) to give the title compound as a solid. Mass spectrum (ES+): 316 (M+H).

Provenance & Evidence