Methyl 3-(butylamino)-4-nitrobenzoate → Methyl 4-amino-3-(butylamino)benzoate

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A solution of methyl 3-(butylamino)-4-nitrobenzoate (1.1 g) and 10% Pd/C (110 mg) in methanol (20 mL) was shaken under an atmosphere of hydrogen at 50 psi for 2 h. The mixture was filtered through diatomaceous earth, and concentrated under reduced pressure to provide 940 mg of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 7.13, 6.94, 6.52, 3.72, 3.02, 1.60, 1.42, 0.93.

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