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

Participants

Reaction Steps

To a suspension of [6-fluoro-3-methyl-4-(4-nitro-phenyl)-naphthalen-2-yl]-acetic acid methyl ester (190 mg, 0.54 mmol) in methanol (3 mL) was added THF (2 mL). Then, zinc dust (287.1 mg, 4.4 mmol), and ammonium chloride (287.8 mg, 5.38 mmol) were added followed by water (1.3 mL). The reaction mixture was stirred at room temperature for 30 minutes. Solid was filtered and washed with ethyl acetate (20 mL). The solution was concentrated to remove organic solvent, and then diluted with water (25 mL). 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-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (118 mg, 67.7%) as a light brown solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.71-7.83 (m, 1 H), 7.69 (s, 1 H), 7.27 (s, 1 H), 7.10-7.22 (m, 1 H), 6.93-7.09 (m, 3 H), 6.83 (d, J=7.8 Hz, 1H), 3.86 (s, 2 H), 3.78 (br. s, 2 H), 3.74 (s, 3 H), 2.19 (s, 3 H). HRMS calcd. for C20H19FNO2 [(M+H)+] 324.1395, obsd. 324.1392.

Provenance & Evidence