[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[C:3]=1[N+:9]([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C>[NH2:9][C:3]1[C:4]([OH:8])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1]4-chloro-3-nitro-pyridin-2-ol (1.69 g, 9.72 mmol) and tin tetrachloride dihydrate (SnCl2.2H2O) (10.97 g, 48.62 mmol) was dissolved in ethanol (32 ml), heated to 70□ and stirred for 2 hours. The reaction mixture was cooled to room temperature and the ethanol was evaporated under reduced pressure. The residue was neutralized with saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain pale-yellow solid (650 mg, 46%).
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