3-Phenylindole → 3-phenyl-2,3-dihydro-1H-indole

Participants

Reaction Steps

8.0 G of 3-phenylindole was dissolved in 120 ml of 96% ethanol and 60 ml of 48% hydrofluoroboric acid was added thereto. 0.4 G of platinum oxide was added to the mixture which was hydrogenated at 30 p.s.i. at room temperature for four hours. The catalyst was removed by filtration, the filtrate concentrated to 1/3 of the volume, basified with 50% aqueous sodium hydroxide and then extracted with ether. 6.7 G of a dark oil which was obtained from the ether extracts after removal of the solvent was chromatographed on silica gel to give 4.1 g of 3-phenylindoline as a pale yellow viscous oil.

Provenance & Evidence