Methyl 2-methyl-3-nitrobenzoate → 3-Amino-2-methylbenzoic acid methyl ester

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A mixture of methyl 2-methyl-3-nitrobenzoate (30 g, 154 mmol), 10% palladium on charcoal (3.0 g) and ethanol (350 mL) was shaken under hydrogen at 50 psig. After 4 h, the mixture was filtered through Celite® and the solids were washed with additional ethanol. The filtrate was concentrated to provide the title product (24.4 g, 96%) as a tan oil: 1H NMR (CDCl3) δ 7.18 (m, 1H), 7.06 (m, 1H), 6.78 (m, 1H), 3.85 (s, 3H), 2.34 (s, 3H); high resolution mass spectrum (NH3 --CI) calculated (M+H+) 166.0868, found 166.0866.

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