[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[NH2:13].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Zn+2].[Cl-]>[NH2:13][C:5]1[CH:6]=[N+:7]([O-:10])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]4-Nitropyridine N-oxide (140 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25° C. After completion of the addition, the resulting mixture was stirred at 25° C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography [eluent: ethyl acetate] to obtain 58 mg of 3-amino-4-nitropyridine N-oxide (yield: 38%).
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