Piconol → 8-Hydroxy-2-methyl-4-(2-pyridylmethoxy)quinoline

Participants

Reaction Steps

To an ice-cooled solution of 2-hydroxymethylpyridine (164 mg) in anhydrous dimethylimidazolinone (2 ml) was added sodium hydride (40% in oil, 100 mg), and the mixture was stirred at the same temperature for 30 minutes. To this mixture were added 4-chloro-8-hydroxy-2-methylquinoline (194 mg) and tetrabutylammonium iodide (185 mg). The mixture was stirred at 100° C. for 8 hours and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water three times, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography (n-hexane-ethyl acetate) followed by trituration with n-hexane to give 8-hydroxy-2-methyl-4-(2-pyridylmethoxy)quinoline (131 mg) as a pale yellow powder.

Provenance & Evidence