[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[CH:6][CH:7]=1A mixture of 1-(4-fluorophenyl)-4-nitropyrazole (0.820 g, 3.96 mmol) and 10% Pd/C (0.133 g, 50% wet by wt) in EtOH (50 mL) was fitted onto a Parr apparatus and agitated under H2 at 40 psi for 40 min. The reaction mixture was then filtered through filter paper. The filtrate was collected and concentrated in vacuo to give 1-(4-fluorophenyl)pyrazol-4-amine as an oil (0.675 g, 96%).
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