Acetonitrile → [4-(4-Acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid

Participants

Reaction Steps

To a solution of [4-(4-acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (112 mg, 0.29 mmol) in ethanol (3 mL) and THF (3 mL) was added a sodium hydroxide solution (586 uL, 1.0 N) at room temperature. The resulting clear solution was stirred for 4 h. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL), acidified with 1.0 N hydrochloric acid, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (20 mL) and dried over anhydrous magnesium sulfate. Filtration of drying agent and concentration of the solvent under vacuum gave a solid which was treated with hot acetonitrile. After cooling in the refrigerator, the solids were collected by filtration and washed with acetonitrile to give [4-(4-acetylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid (65 mg, 60.2%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.50 (s, 1 H), 10.13 (s, 1 H), 7.93 (d, J=8.8 Hz, 1 H), 7.84 (s, 1 H), 7.76 (d, J=8.2 Hz, 2 H), 7.45 (dd, J=8.8, 1.8 Hz, 1 H), 7.15 (m, 3 H), 3.84 (s, 2 H), 2.10 (br. s., 3 H), 2.09 (br. s., 3 H). HRMS (ES+) calcd. for C21H19ClNO3 [(M+H)+] 368.1048, obsd. 368.1049.

Provenance & Evidence