Diethyl Oxalate → Ethyl (4-fluoroanilino)(oxo)acetate

Participants

Reaction Steps

Diethyloxalate (133 g) and p-fluoroaniline (100 g) were refluxed together for 2 hours, during which time the temperature dropped from 160° to 100°. The dark coloured mixture (with suspended crystalline solid) so produced was allowed to cool to 90°, and then diluted with ethanol (100 ml). After cooling overnight, the crystalline product was filtered off and washed thoroughly with cyclohexane. The white solid so obtained, was thoroughly dried to give ethyl 4'-fluorooxanilate (114 g; 60% yield), m.p. 117°-119° (with softening at 116°).

Provenance & Evidence