[CH3:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][CH:3]=1.[ClH:9].N([O-])=O.[Na+].[S:14]([O-:17])(O)=[O:15].[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([S:14]([Cl:9])(=[O:17])=[O:15])=[CH:4][CH:3]=1
To a mixture of 6-methylpyridine-3-amine (449 mg) and concentrated hydrochloric acid (5 mL) was added a solution of sodium nitrite (857 mg) in water (2 mL) at 0° C., and the mixture was stirred at the same temperature for 10 min. To the mixture was added a solution of concentrated hydrochloric acid (2.5 mL), copper sulfate (69 mg) and sodium hydrogen sulfite (5.08 g) in water (8 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=10:1) to give the title compound as a pale-yellow solid (yield 0.12 g, 15%).
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