Hydrochloric Acid → HCID 86657977, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (36.9 g, 97.4 mmol) in ethanol (200 mL)/1-methylpyrrolidin-2-one (50 mL) were added 1N hydrochloric acid (50 mL) and reduced iron (27.2 g, 487 mmol), and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was diluted with ethyl acetate (200 mL), and 2N aqueous sodium hydroxide solution (50 mL) was added. The insoluble material was filtered off through a celite pad, and the insoluble material was washed with ethyl acetate (1 L). Benzyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (38.3 g, 101 mmol) was treated in the same manner as above. The obtained filtrates were combined, washed with saturated brine (3×200 mL), and purified by silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure, and the crystals precipitated during concentration were collected by filtration to give the title compound (56.6 g, 82%) as a pale-orange solid.

Provenance & Evidence