Stannous chloride dihydrate → 5-Amino-1-chloroisoquinoline

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A solution (40 ml) of 1-chloro-5-nitroisoquinoline (2.23 g, synthesized according to the method described in J. Med. Chem. 45, 3, 740 (2002)) in ethyl acetate was added with tin(II) chloride dihydrate (12.39 g, Wako Pure Chemical Industries) at room temperature and stirred with heating at 70° C. for 1 hour. The reaction mixture was cooled to room temperature, then added with ice (200 g) and stirred for 0.5 hour. The reaction mixture was filtered through Celite and extracted three times with ethyl acetate (200 ml for each time), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (749 mg).

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