Hydrochloric Acid → 8-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Participants

Reaction Steps

A mixture of commercially available compound 10, 8-quinolinol (7.3 g, 50.29 mmol), 8 mL of 32% HCl in water, and 8 mL of 37% formaldehyde in water at 0° C. was treated with hydrogen chloride gas for 6 h. The solution was allowed to stand at room temperature for 2 h without stirring. The yellow solid obtained was collected on a filter, washed with 90% alcohol, and dried under vacuum to give 5-chloromethyl-8-quinolinol hydrochloride 11 as yellow solid (9.0 g, 77.78%). 1H NMR of HCl salt (400 MHz, DMSO) δ ppm 5.30 (s, 2H), 7.49-7.51 (d, 1H, J=8 Hz), 7.83-7.85 (d, 1H, J=8 Hz), 8.08-8.12 (dd, 1H, J1=5.6 Hz, J2=8.8), 9.098-9.110 (d, 1H, J=4.8 Hz), 9.193-9.213 (d, 1H, J=8 Hz)

Provenance & Evidence