Water → HCID 58158506, compound

Participants

Reaction Steps

To a solution of benzyl {4-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (5.99 g, 16.4 mmol) in ethanol (80 mL)/water (16 mL) were added reduced iron (5.8 g, 98.4 mmol) and calcium chloride (1.42 g, 11.5 mmol), and the mixture was heated under reflux for 16 hr. The reaction mixture was cooled to room temperature, filtered through celite, and washed with ethanol. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate (50 mL) was added to the residue, and the mixture was extracted with ethyl acetate (150 mL). The organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, a solid was precipitated with hexane/ethyl acetate (=2/1, 30 mL) and collected by filtration to give the title compound (4.43 g, 81%). The solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (NH silica, hexane/ethyl acetate=3/1→1/3) to give the title compound (0.43 mg, 8%).

Provenance & Evidence