Hydrochloric Acid → N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

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To a solution of N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (840 mg, 2.36 mmol) in ethanol (100 mL) was added iron powder (11.9 g, 212 mmol) with heating under reflux. The obtained suspension was vigorously stirred, and 6N hydrochloric acid (50 mL) was slowly added dropwise. The reaction mixture was refluxed for 2 hr with vigorous stirring, and excess iron powder was filtered off through celite. The filtrate was concentrated to about 50 mL, and the residue was diluted with ethyl acetate (250 mL), washed with 1N aqueous sodium hydroxide solution (100 mLx2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (833 mg) as a pale-yellow solid.

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