Glycerol → 2,3-Dihydro4-(2-dimethylaminoethyl)-4H-pyrido[2,3-g][1,4]benzoxazine

Participants

Reaction Conditions

Reaction Steps

6-Amino-3,4-dihydro-4-(2-dimethylaminoethyl)-2H-1,4-benzoxazine (D3, 4.66 g, 21 mmol), glycerol (2.9 g, 31 mmol) and iodine (0.135 g, 0.5 mmol) were stirred as conc. H2SO4 (3.2 ml, 60 mmol) was cautiously added. The mixture was stirred at 180° C. for 2 h, cooled, dispersed in water (300 ml), basified (40% NaOH), and extracted with dichloromethane. The extract was dried (Na2SO4) and evaporated to an oil, which was chromatographed on silica, eluting with 20% methanol/dichloromethane. This gave the title compound (0.50 g, 9%) as a dark oil.

Provenance & Evidence