N,N-Diethylethylenediamine → N-[2-(diethylamino)ethyl]-6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxamide

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Reaction Steps

This compound was prepared, starting from compound 99 (2.00 g, 6.08 mmol) and N,N-diethylethylenediamine (1.21 mL, 8.56 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 14 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 96/4, v/v) to give compound 100 (2.17 g, 5.25 mmol) as a beige solid. Yield 86%; Rf (Al2O3, CH2Cl2/EtOH, 96/4, v/v) 0.51; mp 141-143° C.; IR (KBr) ν 1392, 1491, 1560, 1617, 1641, 2800-3000, 3293 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.07 (t, 6H, J=7.1 Hz), 2.62 (q, 4H, J=7.1 Hz), 2.71 (t, 2H, J=6.3 Hz), 3.50 (m, 2H), 6.30 (d, 1H, J=7.5 Hz), 7.64 (m, 2H), 8.07 (d, 1H, J=1.9 Hz), 8.79 (d, 1H, J=1.9 Hz); ESI-MS m/z 413.8 [M+H]+.

Provenance & Evidence