[(4-Methoxy-2-nitrophenyl)imino]ethyl acetate → 7-Methoxy-3,4-dihydroquinoxalin-2(1H)-one

Participants

Reaction Steps

The obtained [(4-methoxy-2-nitrophenyl)imino]ethyl-acetate crude product was dissolved in methanol (30 ml) and 10% palladium on carbon (50% wet, 1.20 g) was added thereto and the mixture was stirred at room temperature for 3 hours under a hydrogen gas atmosphere. The catalyst was removed by filtration using celite and the filtrate was concentrated under reduced pressure to yield 1.733 g of a crude product of 7-methoxy-3,4-dihydroquinoxalin-2(1H)-one. In dichloromethane (12 ml) was dissolved 518 mg of the obtained crude product of 7-methoxy-3,4-dihydroquinoxalin-2(1H)-one, and under a nitrogen gas atmosphere in an ice bath, N,N-diisopropylethylamine (0.604 ml, 3.47 mmol) and subsequently benzyl chloroformate (0.408 ml, 2.77 mmol) were added thereto. Then, the mixture was stirred at room temperature for 17 hours, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the resultant was extracted with dichloromethane. The extract was combined, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 291 mg (40%) of the title compound in the form of a light red solid.

Provenance & Evidence