Ethyl Acetate → (4-Amino-3'-chloro-biphenyl-3-yl)-dimethyl-methanol

Participants

Reaction Steps

To a solution of 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (.55 g, 2.2 mmol) in anhydrous THF under nitrogen was added a solution of methyl magnesium bromide (3.0 M in diethyl ether, 1 mL, 3 mmol) at 0° C. The mixture was slowly warmed to room temperature and kept stirring under nitrogen for 18 hours. The mixture was treated with 10 mL of saturated ammonium chloride aqueous solution and ethyl acetate (50 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (20 mL) and dried (MgSO4). After removal of the solvent, the residue was purified by a flash chromatography (silica gel, hexane:ethyl acetate/2:1) to afford the title compound as an off-white solid: 186-188° C. (HCl salt). Anal. Calc. For C15H17Cl2NO: C, 60.42, H, 5.75, N, 4.7. Found: C, 60.51, H, 5.62, N, 4.56.

Provenance & Evidence