4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-3-carboxamide → 4-chloro-N-[2-(diethylamino)ethyl]-6-iodoquinoline-8-carboxamide

Participants

Reaction Steps

This compound was prepared, starting from compound 100 (2.00 g, 4.84 mmol), according to the procedure developed for compound 95. Reaction time at 100° C.: 15 min; the purification was performed using column chromatography (Al2O3, AcOEt/cyclohexane, 9/1, v/v) to give compound 101 (1.52 g, 3.52 mmol) as a beige solid. Yield 73%; Rf (Al2O3, AcOEt/cyclohexane, 9/1, v/v) 0.49; mp 76-78° C.; IR (KBr) ν 1555, 1654, 2962 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.09 (t, 6H, J=7.1 Hz), 2.64 (q, 4H, J=7.1 Hz), 2.75 (t, 2H, J=6.4 Hz), 3.66 (q, 2H, J=6.4 Hz), 7.54 (d. 1H, J=4.7 Hz), 8.68 (d, 1H, J=2.1 Hz), 8.76 (d, 1H, J=4.7 Hz), 9.07 (d, 1H, J=2.1 Hz), 11.01 (m, 1H); MS m/z 433 (M+2, 1), 431 (M+, 1), 360 (1), 358 (1), 317 (1), 315 (3), 289 (1), 287 (1), 191 (1), 189 (2), 161 (3), 126 (2), 99 (9), 86 (100), 71 (2), 58 (9).

Provenance & Evidence