Ammonium Chloride → HCID 18969218, compound

Participants

Reaction Steps

Zinc (4.4 g, 67 mmol) was added to a mixture of 1-methyl-4-(3-nitrophenyl)-1,8-naphthyridin-2(1H)-one (0.95 g, 3.4 mmol) obtained in Example 12, methanol (20 ml) and an aqueous solution (20 ml) of ammonium chloride (3.6 g, 67 mmol) under ice-cooling, and the mixture was stirred for 4 hours under ice-cooling and then for 3 hours at room temperature. After removing insoluble matter by filtration, the filtrate was concentrated under reduced pressure, water was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the resulting filtrate was concentrated under reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate) to give 4-(3-aminophenyl)-1-methyl-1,8-naphthyridin-2(1H)one (693 mg, 82%).

Provenance & Evidence