4-(Methylamino)-3-nitrobenzoic acid → 3-Amino-4-(methylamino)benzoic acid

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Reaction Steps

A mixture of 4-(methylamino)-3-nitrobenzoic acid (29 g, 1.0 eq) and Pd/C (5 g, 10%) in 300 mL MeOH was stirred at rt under hydrogen for 48 h and filtered. The filtrate was concentrated in vacuo to give the product (9 g, 36.5%). 1H NMR (400 MHz, DMSO-d6) δ 7.21 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.14 (d, J=2.0 Hz, 1H), 6.37 (d, J=8.4 Hz, 1H), 5.28 (brs, 1H), 4.60 (brs, 2H), 2.76 (s, 3H).

Provenance & Evidence