[Cl-].[NH4+].O.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:13]=2)=[CH:8][CH:7]=1>[Fe].C(O)(=O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH:15]2[N:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:13]=[C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:11][CH:10]=3)[CH2:16]2)=[CH:18][CH:19]=115.8 g of metallic iron powder and 1.6 g of ammonium chloride were dispersed in a mixed solution of 140 ml of iospropyl alcohol and 14 ml of water, and, while stirring and refluxing under heating, 13.1 g of 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1-phenyl-2-pyrazoline was added thereto. After refluxing for 2 hours, 10 ml of acetic acid was added thereto, and the reaction was thereafter continued for 30 minutes under refluxing. Solids were removed by filtration using sellaite, and 150 ml of water was added to the filtrate. Crystals precipitated were collected by filtration to obtain 9.7 g of 5-(4-aminophenyl)-3-(4-methoxyphenyl)-1-phenyl-2-pyrazoline. m.p. 164°-166° C.
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