Water → [4-(4-Amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Participants

Reaction Steps

To a suspension of [6-chloro-3-methyl-4-(4-nitro-phenyl)-naphthalen-2-yl]-acetic acid methyl ester (133 mg, 0.36 mmol) in methanol (2 mL) was added THF (2 mL). Then, zinc dust (192.1 mg, 2.9 mmol) and ammonium chloride (192.6 mg, 3.6 mmol) were added followed by water (0.9 mL). The reaction mixture was stirred at room temperature for 10 minutes and TLC analysis of the mixture indicated the absence of starting material. The resulting solids were filtered and washed with ethyl acetate (20 mL). The solution was concentrated to remove organic solvent, then diluted with water (20 mL) and the mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (30 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum gave [4-(4-amino-phenyl)-6-chloro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (120 mg, 97.9%) as a light brown oil which solidified slowly. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.90 (d, J=8.7 Hz, 1 H), 7.79 (s, 1 H), 7.43 (dd, J=8.7, 1.9 Hz, 1 H), 7.27 (d, J=1.9 Hz, 1 H), 6.85 (d, J=8.2 Hz, 2 H), 6.72 (d, J=8.2 Hz, 2 H), 5.26 (s, 2 H), 3.93 (s, 2 H), 3.64 (s, 3 H), 2.09 (s, 3 H). HRMS calcd. for C20H18ClNO2 [(M+H)+] 340.1099, obsd. 340.1097.

Provenance & Evidence