[Cl-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([NH:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][O:13]2)[C:7]([N+:17]([O-])=O)=[CH:6][CH:5]=1>C(O)C.O.[Fe]>[NH2:17][C:7]1[C:8]([NH:10][CH2:11][CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[N:9][C:4]([Cl:3])=[CH:5][CH:6]=1To a suspension of 13 g of iron powder in 650 mL of ethanol and 350 mL of water, 14 g of sodium chloride was added, and the mixture was heated under reflux while stirring for 20 minutes. Thereto was added 10 g of 6-chloro-N-(1,3-dioxolan-2-ylmethyl)-3-nitropyridin-2-amine at 65° C., and the mixture was heated under reflux while stirring for 30 minutes. The insoluble substance was filtered off, the solvent was distilled off to be 300 mL under reduced pressure, ethyl acetate was added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using an eluent of ethyl acetate to obtain 6.5 g of 3-amino-6-chloro-2-(1,3-dioxolan-2-ylmethyl)aminopyridine as a light purple solid.
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