Ammonium formate → Methyl 3,4-diamino-2-methylbenzoate

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To a solution of methyl 4-amino-2-methyl-3-nitrobenzoate (1.10 g, 5.22 mmol) in tetrahydrofuran (75 mL) and water (25 mL) was added ammonium formate (6.6 g, 104 mmol) and iron powder (2.92 g, 52.2 mmol). This mixture was refluxed for 12 hours then filtered and the filter cake rinsed with ethyl acetate. The filtrate layers were separated and the organic layer was dried (magnesium sulfate), filtered and concentrated to give 0.92 g (98% yield) of crude methyl 3,4-diamino-2-methylbenzoate, which was used without further purification. 1H NMR (400 MHz, d6-DMSO): 7.05 (d; 1H), 6.40 (d, 1H), 3.69 (s, 3H), 2.29 (s, 3H). MS (EI) for C9H12N2O2: 181 (MH+).

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