Ethyl 2-methyl-3-(4-nitrophenyl)prop-2-enoate → Ethyl 4-amino-alpha-methylcinnamate

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Reaction Steps

Ethyl 4-nitro-α-methylcinnamate (11 g) was dissolved in glacial acetic acid (150 ml), and stirred at room temperature. Then, zinc powder (12 g) was added to the above-mentioned solution over a period of about 1 hour. The mixture was stirred at room temperature for 1 day. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed successively with water, saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure to give ethyl 4-amino-α-methylcinnamate (9 g).

Provenance & Evidence