Acetic Acid → HCID 22349482, compound

Participants

Reaction Conditions

Reaction Steps

(5-Amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol (11.8 g, 21.0 mmole) was dissolved in acetic acid (400 mL) and the resulting mixture was stirred at 95° C. overnight. After completion, the reaction was cooled to room temperature and solvent was removed under vacuum and replaced with methanol. Potassium carbonate (2 g) was added and the mixture stirred at room temperature for 1 hour. The solvent was removed and the residue partitioned between 400 mL each of methylene chloride and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuum. The crude residue was column chromatographed on silica gel using first methylene chloride to remove impurities and then 5% methanol/methylene chloride to elute 2.34 g of the title compound. 1H NMR (DMSO-d6): δ 7.10 (d, 1H); 7.00 (t, 1H); 6.60 (d, 1H); 5.30 (t, 1H); 4.60 (d, 2H); 4.10 (dd, 1H); 3.60 (m, 2H); 2.50 (s, 3H).

Provenance & Evidence