Ammonia → 3,4-Dihydro-2H-1,4-benzoxazine

Participants

Reaction Steps

2H-1,4-benzoxazin-3-(4M-one (4.5 g, 30 mmol) was added portionwise to a stirred suspension of lithium aluminium hydride (4.7 g, 120 mmol) in THF (100 ml) and heated at reflux for 3 h. The mixture was cooled in an ice/water bath and ammonia solution (8 ml) and water (40 ml) were added while stirring. The mixture was filtered through Celite and reduced. Chromatography (50% EtOAc/50% 60-80 petroleum ether) afforded benzomorpholine (3.7 g, 91%) as a pale brown oil.

Provenance & Evidence