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

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Reaction Steps

This compound was prepared, starting from compound 104 (0.34 g, 0.82 mmol), according to the procedure developed for compound 95. Reaction time at 100° C.: 15 min; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 105 (323 mg, 0.75 mmol) as a beige solid. Yield 91%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.42; mp 64-66° C.: IR (KBr) ν 1182, 1297, 1386, 1479, 1518, 1691, 2811, 2965, 3354 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.11 (t, 6H, J=7.1 Hz), 2.66 (q, 4H, J=7.1 Hz), 2.75 (t, 2H, J=6.2 Hz), 3.60 (q, 2H, J=6.1 Hz), 7.82 (d, 1H, J=8.9 Hz), 8.03 (dd, 1H, J=1.8, 8.9 Hz), 8.36 (s, 1H), 8.56 (m, 1H), 8.64 (d, 1H, J=1.8 Hz); ESI-MS m/z 431.8 [M+H]+.

Provenance & Evidence