Water → 7-Methyl-3,4-dihydro-2H-1,4-benzoxazine

Participants

Reaction Steps

A solution of 2-hydroxy-4-methyl aniline (5.0 g, 40 mmol), potassium carbonate (16.56 g, 120 mmol) and 1,2-dibromoethane (3.8 g, 20 mmol) in THF (20 mL) was heated at 100° C. in pressure-gauge-steel vessel for 16 h. The completion of reaction was monitored by LCMS. The reaction mixture was poured into water (40 mL) and extracted with EtOAc (250 mL). The organic layer was dried over sodium sulfate, evaporated and the residue purified by column chromatography to obtain 1.72 g of 3,4-dihydro-7-methyl-2H-benzo[b][1,4]oxazine (free base).

Provenance & Evidence