Water → HCID 58237114, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of p-toluenesulfonic acid hydrate (1.03 g) and toluene (15 mL) was refluxed for 2 h with azeotropic removal of water, and then cooled to 90° C. A solution of ethyl 2-[(2-methoxy-4-{[6-(methoxymethyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (1.0 g) in toluene (10 mL) was added to the mixture at 90° C. The whole was stirred at 90° C. for 1 h, and then refluxed for 2 h. An aqueous solution of sodium hydrogen carbonate was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by basic silica gel chromatography (ethyl acetate:hexane=1:4 to 2:1, volume ratio) and then by silica gel chromatography (ethyl acetate:hexane=1:9 to 2:1, volume ratio) to give the title compound (140 mg, 15%) as pale yellow crystals. MS 357 (MH+).

Provenance & Evidence