Aniline → N,9-Diphenyl-9H-carbazol-3-amine

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL three-neck flask were put 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 340 mg (0.6 mmol) bis(dibenzylideneacetone)palladium(0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium tert-butoxide, and then the atmosphere in the flask was substituted with nitrogen. Thereafter, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added to the mixture. This mixture was heated and stirred for 7.5 hours at 90° C. After the reaction was completed, about 500 mL of hot toluene was added to the reaction solution, and this solution was filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, and hexane and ethyl acetate were added to the residue, which was followed by irradiation with ultrasound. A solid precipitated was collected by suction filtration and dried to give 15 g (75% yield) of N,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA) as light brown powder. By a nuclear magnetic resonance measurement (NMR), this compound was determined to be N,9-diphenyl-9H-carbazol-3-amine (abbreviation: PCA).

Provenance & Evidence