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

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL three-neck flask were added 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 0.34 g (0.60 mmol) of bis(dibenzylideneacetone)palladium(0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (0.18 mol) of sodium tert-butoxide, and the atmosphere in the flask was substituted with nitrogen. Then, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added thereto. This was heated and stirred at 90° C. for 7.5 hours under a stream of nitrogen. After the reaction was completed, about 500 mL of hot toluene was added to the reaction solution, followed by filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The obtained filtrate was concentrated, and hexane and ethyl acetate were added thereto, followed by irradiation with ultrasonic waves, whereby a solid substance was precipitated. This solid substance was collected by suction filtration and dried to produce 15 g (75% yield) of N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA) as a milky white powder. By a nuclear magnetic resonance method (NMR), this compound was proved to be N-phenyl-(9-phenyl-9H-carbazol-3-yl)amine (abbreviation: PCA).

Provenance & Evidence