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

反応式

[CH3:1][C:2]1([CH3:16])[C:7](=O)[NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.Cl>C1COCC1.CO>[CH3:1][C:2]1([CH3:16])[CH2:7][NH:6][C:5]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1

参加物

実験手順

2,2-Dimethyl-6-nitro-4H-benzo[1,4]oxazin-3-one was added to BH3-THE 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.