[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH:12]1[CH:13]=[CH:14][C:10]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)=[N:11]1To a solution of 3-(3-nitrophenyl)-1H-pyrazole 12.A (490 mg, 2.59 mmol, available from Oakwood) in methanol (5 mL) was added 10% Pd on carbon by weight (100 mg). The air was evacuated from the reaction flask and was replaced with hydrogen. The resulting slurry was stirred overnight at room temperature. The reaction mixture was filtered, and the mother liquor condensed to afford 3-(1H-pyrazol-3-yl)benzenamine 12.B (397 mg, 96% yield).
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