Hydrochloric Acid → N-{4'-methyl-[1,1'-biphenyl]-2-yl}acetamide

Participants

Reaction Steps

A stirred solution of 4′-methyl-1,1′-biphenyl-2-amine (3.09 g, 16.87 mmol) in dichloromethane was treated with acetic anhydride (1.75 mL, 18.6 mmol), pyridine (3.14 mL, 38.8 mmol), and 4-(N,N-dimethylamino)pyridine (0.062 g, 0.506 mmol). After stirring under argon for 16 hours, a saturated, aqueous, ammonium chloride solution (5 mL) was added to the reaction mixture and stirring continued another 30 minutes. The reaction mixture was poured into a 0.1 N hydrochloric acid solution. The separated aqueous phase was further extracted with dichloromethane (3×). The combined organic phase was washed sequentially with a 0.1 N hydrochloric acid solution and a saturated aqueous, sodium bicarbonate solution. After drying over anhydrous magnesium sulfate, the solvent was removed in vacuo. The crude product was purified by re-crystallization from a mixture of ethyl acetate-hexane to yield the title compound (3.17 g, 14.1 mmol, 83%) as a white, crystalline solid;

Provenance & Evidence