[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.CO[NH2:14].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O.[Cl-].[Zn+2].[Cl-]>[NH2:14][C:7]1[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=16-Methoxy-3-nitropyridine (154 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMSO (2 ml), and a resulting solution was added dropwise to a DMSO 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 9 hours 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 subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1] to obtain 147 mg of 2-amino-6-methoxy-3-nitropyridine (yield: 87%).
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