Methanol → 2-Propenoic acid, 3-(4-aminophenyl)-, methyl ester

Participants

Reaction Steps

4-Aminocinnamic acid (15.0 g, 77.6 mmol) was added to a mixed solvent of methanol (250 ml) and chloroform (150 ml), and sulfuric acid (3 ml) was added, which was followed by refluxing under heating for 47 hours. The reaction mixture was concentrated under reduced pressure, and the residue was made weak alkaline with a saturated aqueous sodium hydrogencarbonate and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure to give 7.84 g of methyl 4-aminocinnamate as a yellow solid (72%). This solid (7.80 g, 44.1 mmol) was dissolved in methanol (250 ml) and 10% palladium-carbon (780 mg) was added. The mixture was stirred at room temperature for 19 hours under a hydrogen atmosphere. The reaction mixture was filtered through Celite and low boiling matters were distilled away from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to give 5.98 g of methyl 3-(4-aminophenyl)propionate as a colorless solid (76%).

Provenance & Evidence