Urea → 2-Ethyl-5-nitrophenol

Participants

Reaction Conditions

Reaction Steps

A solution of 2-ethyl-5-nitroaniline (prepared as described by E. Dyszer et al, Przemysl. Chem 42 (8) 433-5 (1963)) (5 g) in concentrated sulphuric acid (27 ml) and water (160 ml) at 0° C., was treated with sodium nitrite (2.3 g) in water (5 ml) over 5 minutes with stirring. After 1/4 h at 0° C., urea (2 g) was added and the mixture heated to 80° C. for 2 h. After stirring overnight at room temperature, the pH was adjusted to pH 10-12 with 10% sodium hydroxide, and the mixture extracted into ethyl acetate. The organic phase was dried (Na2SO4) and the solvent evaporated under reduced pressure. Flash column chromatography on silica gel, eluting with ethyl acetate and 60°-80° C. petroleum-ether gave the title compound (2.91 g, 58%).

Provenance & Evidence