1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanone → HCID 46214905, compound

Participants

Reaction Steps

To a solution of 1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanone (550 mg, 1.8 mmol) in methanol (10 ml) at room temperature was added portionwise sodium borohydride (315 mg, 8.3 mmol). After the addition the reaction was stirred for 3 hours. Most of the solvent was removed under reduced pressure, the residue diluted with ethyl acetate, and the mixture was poured into a separatory funnel. The organic layer was washed with water (2×), saturated sodium bicarbonate, then brine. The organic phase was separated and solvent removed under reduced pressure to provide 1-(6-chloro-2-methyl-4-phenylquinolin-3-yl)ethanol (460 mg, 83%) as a white powder. TLC Rf=0.4 using 1:1 ethyl acetate:hexanes as eluent. 1H NMR (CDCl3, 400 MHz) δ 7.88 (d, 1H, J=8.9 Hz); 7.54-7.42 (m, 4H); 7.18-7.08 (m, 3H); 5.05 (q, 1H, J=7.0 Hz); 2.95 (s, 3H); 1.0 (d, 3H, J=6.65 Hz). LCMS (CI) shows M+H 297.

Provenance & Evidence