4-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide → 1-(4-Chloro-2-phenylamino-phenyl)-propan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-N-methoxy-N-methyl-2-phenylamino-benzamide (5.0 g, 17.2 mmol) in tetrahydrofuran (60 mL) was treated dropwise with ethylmagnesium bromide (1M solution in tetrahydrofuran, 70 mL, 70 mmol). Upon completion of addition, the mixture was allowed to slowly warm to 25° C. where it was stirred for 2 h. At this time, the reaction was cooled to 0° C., was quenched with a 1N aqueous hydrochloric acid solution (50 mL) and was then extracted with ethyl acetate (2×300 mL). The combined organics were washed with water (100 mL) and a saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (silica gel; 100-200 mesh, ethyl acetate/hexanes 10-25%) afforded 1-(4-chloro-2-phenylamino-phenyl)-propan-1-one (4.15 g, 92.9%) as a yellow oil. 1H NMR (DMSO-d6) δ ppm 10.53 (s, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.34-7.51 (m, 2H), 7.28 (d, J=7.7 Hz, 2H), 7.13-7.23 (m, 1H), 7.07 (d, J=1.8 Hz, 1H), 6.82 (dd, J=8.6, 1.9 Hz, 1H), 3.07 (q, J=7.2 Hz, 2H), 1.09 (t, J=7.3 Hz, 3H).

Provenance & Evidence