[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)=[C:6]([N+:15]([O-])=O)[CH:5]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)=[C:6]([NH2:15])[CH:5]=1To a solution of 4-cyclobutylamino-3-nitro-benzoic acid methyl ester (18.959, 56.3 mmol) in ethyl alcohol (300 ml) in a Parr shaker was added 10% Pd/C (0.67 g). The reaction was subjected to an atmosphere of hydrogen (50 psi) until the consumption of hydrogen ceased (2 hours). The reaction mixture was filtered through a pad of Celite® and concentrated to give 15.94 g of 3-Amino-4-cyclobutylamino-benzoic acid methyl ester as a solid.
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