ethyl 2-(4-formyl-2-nitrophenoxy)acetate → 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

(4-Formyl-2-nitrophenoxy)acetic acid ethyl ester (1.9 g) in acetic acid (40 mL) was treated with iron powder (4.2 g) and the mixture was stirred at 60° C. for 0.75 hours, filtered and evaporated to dryness. It was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic fraction was chromatographed on silica gel (ethyl acetate) to give a white solid (0.88 g). MS (−ve ion electrospray) m/e 176 (M−H)−.

Provenance & Evidence