Acetic Acid → 3-(2-Amino-4,5-dimethoxyphenyl)-2-methyl-2-propenoic acid ethyl ester

Participants

Reaction Steps

Into 250 ml of glacial acetic acid, 19.0 g of 3-(4,5-dimethoxy-2-nitrophenyl)-2-methyl-2-propenoic acid ethyl ester were dissolved; and, with 15.0 g of iron powder and 20 ml of ion-exchanged water being added thereto, the mixture was refluxed under heating for 40 minutes. The resulting reaction liquid was filtered out, the filtrate was concentrated under a reduced pressure, and thus obtained residue was dissolved in ethyl acetate. The resulting solution was successively washed with water, a 5% aqueous sodium hydrogencarbonate solution, and a saturated aqueous sodium chloride solution. After this ethyl acetate solution was left on sodium sulfate anhydride for one night so as to be dried, ethyl acetate was evaporated under a reduced pressure, and the resulting residue was recrystallized from a mixed liquid of hexane/ethanol, whereby 12.5 g of the aimed product were obtained (yield: 78%).

Provenance & Evidence