Phosphorus oxychloride → 7-Bromo-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-ethoxy-3-quinolinecarbonitrile

Participants

Reaction Steps

A suspension of 3-bromo-4-ethoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide (630 mg, 1.29 mmol) in 35 mL of acetonitrile was heated to reflux and phosphorous oxychloride (0.80 mL) was added dropwise, via syringe. The reaction mixture was heated at reflux overnight, then cooled to room temperature. The solids were collected by filtration, washed with saturated aqueous sodium bicarbonate. The solids were stirred with saturated aqueous sodium bicarbonate for 1 hour and then collected by filtration, washed with saturated aqueous sodium bicarbonate and water. The solid was recrystallized from methanol and dried in vacuo to provide 225 mg of 7-bromo-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-ethoxy-3-quinolinecarbonitrile as a yellow solid, mp >250° C. 1H NMR (400 MHz, DMSO-d6) δ 1.47 (t, J=7 Hz, 3H), 3.87 (s, 3H), 4.32 (q, J=7 Hz, 2H), 7.45 (s, 1H), 7.82 (s, 1H), 8.16(s, 1H), 8.27 (s, 1H), 8.76 (s, 1H), 10.73 (s, 1H); MS (ES) m/z 466.1, 468.0, 470.1 (M+H)+

Provenance & Evidence