2-Aminophenol → Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Participants

Reaction Steps

Ethyl 2,3-dibromopropionate (24 g, 92 mmol) was added dropwise to a refluxing solution of o-aminophenol (10 g, 92 mmol) and potassium carbonate (15 g, 110 mmol) in acetone (100 ml). After 18 h the mixture was cooled and reduced. Ethyl acetate and water were added and the mixture separated. The organic phase was washed with brine, filtered and reduced. Chromatography (30% EtOAc/70% 60-80 petroleum ether) afforded ethyl benzomorpholine-2-carboxylate (4.5 g, 24%) as a red oil.

Provenance & Evidence