4-Amino-m-cresol → HCID 10042634, compound

Participants

Reaction Steps

3-Butyryl-4-chloro-6-hydroxyquinoline (4.0 g) and 4-amino-m-cresol (2.0 g) were heated together under reflux in 1,4-dioxan (60 ml) for 2 hours. The solvent was evaporated and the residue was dissolved in chloroform and washed successively with 2M HCl, sodium hydrogen carbonate solution (×2) and brine. The organic solution was dried, filtered and evaporated to a brown oil. A quantity of solid material that appeared insoluble in chloroform was combined with the oil and the mixture was chromatographed (silica gel, 2-4% methanol in chloroform) to give 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-6-hydroxyquinoline (1.3 g, 24%) as orange crystals, m.p. 242°-244°.

Provenance & Evidence