4-Methylquinoline → HCID 66588616, compound

Participants

Reaction Steps

4-Methylquinoline (470 mg, 3.3 mmol), (3-bromopropyl)triethylammonium bromide (1.0 g, 3.3 mmol), and 10 mL acetonitrile were stirred at 90° C. in a pressure vessel for 64 h. After cooling down, the solvent was removed under vacuum and the residue was purified by column chromatography (SiO2, gradient from CH2Cl2 to MeOH) to furnish 1-(3-triethylammoniopropyl)-4-methylquinolinium dibromide as a white solid (1.29 g, 88%). 1H NMR (400 MHz, CD3OD): δ 1.35 (t, J=7.4 Hz, 9 H), 2.54 (m, 2 H), 3.10 (s, 3 H), 3.39 (q, J=7.2 Hz, 6 H), 3.60 (t, J=8.0 Hz, 2 H), 5.18 (t, J=8.0 Hz, 2 H), 8.04 (d, J=6.0 Hz, 1 H), 8.09 (t, 1 H), 8.33 (t, 1 H), 8.61 (d, 1 H), 8.65 (d, 1 H), 9.43 (d, J=6.0 Hz, 1 H); HRMS (FAB+): m/z=365.1581 [M-Br]+ (calcd for C19H30BrN2: 365.1587).

Provenance & Evidence