Hydrochloric Acid → (2-Amino-4-methoxyphenyl)(phenyl)methanone

Participants

Reaction Conditions

Reaction Steps

A solution of phenylmagnesium bromide (6.75 ml, 3M solution in diethyl ether, 20.2 mmol) in diethyl ether (15 ml) was added dropwise to a solution of 2-amino-4-methoxybenzonitrile (1000 mg, 6.75 mmol) in diethyl ether (20 ml) at 0° C. The resulting suspension was heated to reflux for 2 h. The mixture was then cooled to 0° C. and 2N HCl (40 ml) was added very carefully. After complete addition, the mixture was heated to 55° C. for 2 h. Then 3N NaOH (˜20 ml) was added at 0° C. to adjust the pH to 9. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 85:15-70:30) to afford the title compound (1300 mg, 85%) as yellow solid. MS (ESI): 228.4 (M+H)+.

Provenance & Evidence