N-Ethylaniline → Laquinimod

Participants

Reaction Conditions

Reaction Steps

N-ethylbenzenamine (430 mg, 3.55 mmol, 2.00 equiv) was added dropwise to ethyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (500 mg, 1.78 mmol, 1.00 equiv) dissolved in heptane (10 ml). The resulting mixture was heated about 100° C. and the volatiles were removed by distillation over a period of about 7 hours. After cooling to ambient temperature, the resulting crystals were collected by filtration, washed with heptane, and purified by silica gel chromatography (ethyl acetate/petroleum ether 1:3) to afford the title product as a white solid (0.38 g, yield: 60%).

Provenance & Evidence