Hydrochloric Acid → 2,2-Dimethyl-6-nitro-3,4-dihydro-2H-benzo[B][1,4]oxazine

Participants

Reaction Steps

2,2-Dimethyl-6-nitro-4H-benzo[1,4]oxazin-3-one was added to BH3-THF complex (Aldrich) in THF with ice cooling. The mixture was heated to reflux for 2 h then carefully diluted with 12 mL of MeOH and heated to reflux for an additional 1 h. Concentrated HCl (12 mL) was added and heated to reflux for 1 h. The mixture was concentrated and the resulting solid was suspended in a dilute aqueous solution of NaOH (1 M) and extracted with EtOAc (100 mL×4). The organic layers were washed with H2O and dried over MgSO4. Evaporation of solvent gave a yellow solid.

Provenance & Evidence