Sodium Hydroxide → [4-(4-Benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid

Participants

Reaction Steps

To a solution of [4-(4-benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (130 mg, 0.29 mmol) in ethanol (3 mL) and THF (3 mL) was added a solution of sodium hydroxide (879 uL, 1.0 N) at room temperature. The resulting clear solution was stirred overnight. 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 the drying agent and concentration of the solvent under vacuum afforded (115 mg, 91.3%) [4-(4-benzoylamino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 10.46 (s, 1 H), 7.91-8.04 (m, 5 H), 7.86 (s, 1 H), 7.51-7.68 (m, 3 H), 7.47 (dd, J=8.8, 1.8 Hz, 1 H), 7.23 (d, J=8.5 Hz, 2 H), 7.18 (d, J=1.8 Hz, 1 H), 3.85 (s, 2 H), 2.12 (s, 3 H). HRMS calcd. for C26H21ClNO3 [(M+H)+] 430.1205, obsd. 430.1205.

Provenance & Evidence