Ammonium Chloride → (E)-Ethyl 3-(4-aminophenyl)-2-methylacrylate

Participants

Reaction Conditions

Reaction Steps

The obtained ethyl 3-(4-nitrophenyl)-2-methylacrylate (3.5 g) was dissolved in a mixed solvent of water (75 ml), methanol (75 ml), and THF (75 ml). Ammonium chloride (3.05 g) and iron powder (4.2 g) were added thereto, and the obtained mixture was stirred at 50° C. for 4 hours. The iron powder was filtered, and the solvent was distilled off under reduced pressure. Methanol was added to the obtained residue, and insoluble substances were filtered off. The filtrate was separated with ethyl acetate and water. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (3% chloroform/methanol) to obtain Compound 13a (1.8 g, 32%) as an orange liquid.

Provenance & Evidence