Stannous Chloride → 2-(4-amino-2-chlorophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione

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Reaction Conditions

Reaction Steps

To a stirred solution of 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione (0.106 g, 0.341 mmol) in ethanol (5 mL) was added tin (II) chloride (0.323 g, 1.70 mmol) and the reaction mixture was heated at 80° C. for 15 h. The reaction was cooled to room temperature, quenched with sat. NaHCO3, and the white precipitate was filtered. The filtrate was partitioned between ethyl acetate (20 mL) and brine (15 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated to give the crude product. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 70% to give 84 mg of 2-(4-amino-2-chlorophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]oxazine-1,3(2H)-dione, 1.2.21, (88%).

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