Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17].[NH3:19]>C(O)C>[NH2:19][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[N+:16]([O-:18])=[O:17]A mixture of 5 g of 6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one, 50 ml of 25% aqueous NH3 solution and 50 ml of ethanol is heated at 100° for 16 hours. The mixture is poured into ice water and extracted with methylene dichloride, the phases are separated and the organic phase is dried over sodium sulfate and evaporated to give 6-(4-amino-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one, m.p. 234°-238°.
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