[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-])=O.[ClH:14]>CCO.[Pd]>[ClH:14].[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH3:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]A slurry of 5-nitro-2-methyl-benzoic acid (17.1 g, 94.4 mmol) and 10% Pd/C (500 mg) in EtOH (500 mL) was shaken under 40 psi H2 at ambient temperature for 4 hours. HCl was added and the solution filtered through a pad of celite. The filtrate was concentrated in vacuo to give the title compound (17.2 g).
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