6-(Benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one → 6-Amino-1-isopropyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Participants

Reaction Steps

Palladium on activated carbon (10%, 276 mg, 259 μmol) was added to a solution of 6-(benzylamino)-1-isopropyl-3,3-dimethylindolin-2-one (1.60 g, 5.18 mmol) in ethanol (75 ml). The mixture was stirred at room temperature under an hydrogen atmosphere (balloon) for 16 hours. As reaction was incomplete, the catalyst was filtered off and washed with ethanol. The solvent was evaporated and ethanol (75 ml) was added to the residue. Palladium on activated carbon (276 mg, 259 μmol) was added and hydrogenation (balloon) continued for 6 hours at 50° C. and 12 hours at room temperature. The catalyst was filtered off, washed with ethanol and the solvent was evaporated. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as light yellow solid (892 mg).

Provenance & Evidence