Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:12][NH2:13])=[N:3][CH:4]=1)([O-:10])=[O:9]To a solution of 2-chloro-5-nitropyridine (30 mmol, 5.0 g) in absolute ethanol was added a solution of hydrazine hydrate (320 mmol, 15.8 g) in ethanol using syringe pump. At the end of the addition, the reaction was refrigerated. The named product precipitated from the reaction medium, was collected by filtration, and recrystallized from ethanol.
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