[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)[CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[N:14]1([C:9]2[CH:10]=[N:11][C:12]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[C:4]([NH2:1])[CH:13]=3)[CH:18]=[CH:17][CH:16]=[N:15]1A methanol (10 ml) solution containing 7-nitro-3-(1H-pyrazol-1-yl)quinoline (36 mg) was prepared and subjected to a hydrogenation reaction (80° C.; 50 bar; flow rate: 1 ml/min; 10% Pd/C) using H-cube™. Thereafter, the solvent was distilled away under reduced pressure, and a purple solid of 3-(1H-pyrazol-1-yl)quinolin-7-amine (20 mg) was thus obtained.
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