Formaldehyde → HCID 178503658, compound

Participants

Reaction Steps

To a stirred suspension of 4-hydroxy-8-methylquinoline (10.0 g.) in triethylamine (8.8 ml.) and industrial methylated spirit (15 ml.) at 0°-5° was added methanethiol (10.4 ml.) followed by aqueous formaldehyde (40%, 14.2 ml.). The mixture was stirred and boiled under reflux for 30 hours. Aqueous formaldehyde (40%, 14.2 ml.) was added dropwise to a stirred solution of triethylamine (8.8 ml.) and methanethiol (10.4 ml.) in ethanol (15 ml.), maintaining the temperature below 10°. The resulting solution was added to the above reaction mixture and the mixture was stirred and boiled under reflux for 20 hours. The mixture was left to cool overnight. The resulting crystalline solid was collected by filtration to give the novel compound 4-hydroxy-8-methyl-3-methylthiomethylquinoline, m.p. 226°-228°.

Provenance & Evidence