Hydrochloric Acid → (2-Amino-5-chloro-phenyl)-(2-methyl-pyridin-4-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of boron trichloride (9.35 ml, 9.35 mmol) in 1,1,2,2-tetrachloroethane at 0° C. was added 4-chloroaniline (1.19 g, 9.35 mmol) and the mixture was stirred for 30 minutes. 2-methyl-isonicotinonitrile (920 mg, 7.79 mmol) and aluminum chloride (1.14 g, 8.57 mmol) were added successively and the mixture was heated to reflux for 20 h. The reaction mixture was cooled to 0° C., 2N HCl (20 ml) was added and the mixture was heated to 80° C. for 30 minutes. The mixture was basified with 3N NaOH and extracted with EtOAc. The combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, dichloromethane/EtOAc 95:5 to 100:0) to afford the title compound (390 mg, 20%) as yellow solid. MS (ESI): 247.4 (M+H)+.

Provenance & Evidence