Methanol → 7-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Participants

Reaction Steps

A suspension of 7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (300 mg, 1.545 mmol) in THF (3 mL) was treated with BH3-THF complex (15.45 mL, 15.45 mmol, 1.0 M in THF), and the resulting orange solution was refluxed overnight. The reaction was cooled in an ice-bath. MeOH (15 mL) was added, and the reaction was then concentrated. A second portion of MeOH (20 mL) was added, and the solution was refluxed for 2 hours. At this time, the reaction was concentrated, and the residue was subjected to flash chromatography on silica gel (10% EtOAc:90% hexane followed by 30% EtOAc:70% hexane). An orange solid was obtained after drying under reduced pressure. (240 mg, 86%). 1H-NMR (DMSO-d6) δ 7.68 (dd, J=2.4, 8.9 Hz, 1H), 7.54 (s, 1H), 7.47 (d, J=2.4 Hz, 1H), 6.63 (d, J=9.0 Hz, 1H), 4.15 (t, J=4.2 Hz, 2H), 3.45-3.40 (m, 2H).

Provenance & Evidence