tert-Butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropanecarboxylate → tert-Butyl 1-[(3-amino-4-chlorophenyl)(hydroxy)methyl]cyclopropanecarboxylate

Participants

Reaction Steps

2.72 g (8.30 mmol) of tert-butyl 1-[(4-chloro-3-nitrophenyl)(hydroxy)methyl]cyclopropane-carboxylate were dissolved in 100 ml of ethyl acetate, and 177 mg of palladium on carbon (10%) were added. For three days, the reaction mixture was stirred vigorously under a stationary atmosphere of hydrogen at atmospheric pressure. The mixture was then filtered through Celite and the filtrate obtained was evaporated to dryness. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 1.97 g of the target compound (80% of theory).

Provenance & Evidence