[H][H].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-])=O)=[N:11]2)=[CH:6][CH:5]=1>[Pt].C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[NH2:23])=[N:11]2)=[CH:8][CH:9]=1At 20-25° C. and a hydrogen pressure of 20 bar, a mixture of 30 g (90 mmol) of 2-[1-(4-chlorophenyl)pyrazol-3-yl]oxymethylnitrobenzene and 2 g of platinum on activated carbon (5%) in 200 ml of ethyl acetate was hydrogenated with stirring for approximately 20 hours. The mixture was filtered through Al2O3 and the solvent was removed from the filtrate by distillation, giving 23.3 g of the aniline as yellow crystals of m.p. 81-83° C.
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