Methyl 4-fluoro-5-methyl-2-nitrobenzoate → Methyl 2-amino-4-fluoro-5-methylbenzoate

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The solution of crude methyl 4-fluoro-5-methyl-2-nitrobenzoate (5 g) in MeOH (50 mL) was hydrogenated using 10% Pd/C (0.5 g) as catalyst at atmospheric pressure overnight. The catalyst was removed by filtration, and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (8:1) to give methyl 2-amino-4-fluoro-5-methylbenzoate (2.21 g, yield 50% over three steps) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.715 (d, J=9.0 Hz, 1H), 6.339 (d, J=11.5 Hz, 1H), 3.873 (s, 3H), 2.154 (s, 3H) ppm.

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