Glycerol → 8-Methylquinoline-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of concentrated sulfuric acid (21.74 ml) in water (16 ml), was added 3-amino-2-methylbenzoic acid (5 g; supplier Acros), 1,2,3-propanetriol (2.437 ml) and sodium iodide (0.104 g). The reaction mixture was heated to reflux for 2 hours at 150° C. Further 1,2,3-propanetriol (2.437 ml) was added and reaction mixture was refluxed for another two hours. The pH of the reaction mixture was adjusted to pH 3 by adding sodium hydroxide (12.5 M, 32.6 ml) then the mixture was filtered and the solid discarded. The aqueous phase was extracted with ethyl acetate and then the organic solvent was removed under vacuum to give crude product. This was dissolved in 1:1 DMSO & MeOH and purified by reverse phase chromatography and relevant fractions were combined and concentrated to afford the title compound (750 mg) as a white solid.

Provenance & Evidence