[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[Na].[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([NH:17][NH2:18])=O)=[CH:13][CH:12]=1>CO>[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]2[N:2]=[C:1]([C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)[NH:18][N:17]=2)=[CH:13][CH:12]=1To 4-cyanopyridine (4.2 g.) in methanol (60 ml.) is added sodium (0.2 g.). The solution is allowed to stand for 0.5 hour at room temperature and is then added to a suspension of p-aminobenzhydrazide (6.4 g.) in 150 ml. of methanol. The resulting solution is heated 20 hours at reflux during which time a solid separates. The solid is filtered and heated to 245° C. over one hour and maintained at that temperature for an additional 15 minutes. After cooling the solid is recrystallized from a mixture of acetonitrile and water to yield 3-(p-aminophenyl)-5-(4-pyridyl)-1,2,4-triazole (2 g.) m.p. 251°-252.5° C.
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