Water → N-[6-(4-amino-2-fluorophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

Participants

Reaction Steps

To a suspension of N-[6-(2-fluoro-4-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (1.15 g, 3.07 mmol) in ethanol (50 mL)/water (10 mL) were added ammonium chloride (1.64 g, 30.7 mmol) and reduced iron (856 g, 15.3 mmol), and the mixture was heated under reflux for 4 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with a mixed solution of ethanol/water. The solvent was evaporated under reduced pressure, 1N aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted 3 times with ethyl acetate/tetrahydrofuran. The combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate/diisopropyl ether and collected by filtration to give the title compound (644 mg, 61%) as a pale-yellow solid.

Provenance & Evidence