Methanol → Methyl 4-methoxy-6-quinolinecarboxylate

Participants

Reaction Steps

To a suspension of 4-chloro-6-quinolinecarbonitrile (910 mg) in methanol (50 ml) was dropwise added slowly concentrated sulfuric acid (5 ml) while stirring under ice-cooling. The mixture was heated under reflux for 15 hr and concentrated sulfuric acid (10 ml) was added. The mixture was further heated under reflux for 24 hr. An aqueous sodium hydrogencarbonate solution was added thereto under ice-cooling to make the reaction mixture basic. The reaction mixture was extracted once with chloroform. The organic layer was washed once with water and saturated brine, respectively, and dried over magnesium sulfate. The organic layer was concentrated to dryness under reduced pressure to give a white solid. The solid was pulverized by IPE to give the object compound (910 mg) as a white powder.

Provenance & Evidence