Water → HCID 58237114, compound

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonic acid monohydrate (11.8 g) was refluxed in toluene (200 mL) for 2 h with azeotropic removal of water. The mixture was cooled to 110° C. and a solution of ethyl 2-[(2-methoxy-4-{[6-(methoxymethyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (11.58 g) in toluene (50 mL) was added. The mixture was stirred at 110° C. for 5.5 h. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 75/25), followed by basic silica gel column chromatography (ethyl acetate/hexane=10/90 to 50/50, volume ratio) to afford a yellow solid. The solid was washed with diethyl ether to give the title compound (2.32 g, 21%) as a yellow solid. MS 357 (MH+).

Provenance & Evidence