4-Nitrophenol → 4-[[2-Methyl-4-oxo-3,4-dihydro-(2H)-1,3-benzoxazine-2-yl]methoxy]nitrobenzene

Participants

Reaction Steps

Preparation of 4-[2-oxo-propoxy]nitrobenzene—To stirred suspension of K2CO3 (50.0 g, 0.36 mol) in dry DMF (500 mL) was added 4-nitrophenol (25.0 g, 0.18 mol) and stirred for 30 min at 25° C. Chloroacetone (21.5 mL, 0.27 mol) was added to the reaction mixture and stirred for 24 h at 25-30° C. The reaction mixture was filtered through a buchner funnel. The filtrate was poured into water (500 mL) and extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography using EtOAc:Pet. ether (1:2) as eluent to yield the title compound (11.0 g, 31%) as a colourless liquid.

Provenance & Evidence