Sodium Carbonate → HCID 67285003, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-amino-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone (0.5832 g, 3.03 mmol), 1-bromo-2-(2-bromoethoxy)ethane (0.774 g, 3.34 mmol), MeOH (3 mL), and Na2CO3 (0.6432 g, 6.07 mmol) in a pressure vessel was stirred at 150° C. After 1.5 h, the mixture was cooled to rt. To the cooled mixture was added a solution of KOH (1.1066 g, 19.72 mmol) in water (2 mL) and the mixture was stirred at 55° C. After 1 h, the mixture was cooled to rt, poured into ice water (50 mL), and extracted with EtOAc (50 mL×2). The combined organics were washed with brine (50 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a violet solid. The violet solid was purified by column chromatography on a silica gel column using 0 to 100% gradient of EtOAc in hexane as eluent to give 6-morpholino-3,4-dihydro-2H-benzo[b][1,4]-oxazine as a white solid: Mass Spectrum (ESI) m/e=221.2 (M+1).

Provenance & Evidence