Formaldehyde → HCID 178519814, compound

Participants

Reaction Steps

A mixture of 7-fluoro-4-hydroxyquinoline (91.5 g., containing some 5-fluoro isomer), aqueous sodium hydroxide (1.0 N, 666 ml.) and aqueous formaldehyde (37%, 91.5 ml.) was stirred at 35°-37° for 5.5 hours. A further portion of aqueous formaldehyde (37%, 91.5 ml.) was added and stirring continued for 64 hours. The solid product was collected by filtration, added to water (600 ml.) and the mixture acidified to pH 4.0 with concentrated hydrochloric acid. The solid residue was collected, washed with water and dried to give the novel 7-fluoro-4-hydroxy-3-hydroxymethylquinoline, m.p. 295-300 (containing some 5-fluoro isomer). Further product m.p. 295°-300°, was obtained from the alkaline filtrate of the reaction mixture by acidification to pH 4.0 with concentrated hydrochloric acid, and was combined with the first product.

Provenance & Evidence