Cyclohexane ethylacetate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

Participants

Reaction Steps

At room temperature, 500 mg of palladium on carbon (10%) were added to a solution of 6.74 g (23.76 mmol) of tert-butyl(2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate in 200 ml of ethanol and 20 ml of THF, and the mixture was hydrogenated under atmospheric pressure for 12 hours. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 1:1), the reaction solution was filtered through kieselguhr and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 1.40 g (5.47 mmol, 23% of theory) of the title compound.

Provenance & Evidence