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

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 110 mL of dehydrated xylene and 7.0 g (75 mmol) of aniline were added to a mixture of 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 340 mg (0.6 mmol) of 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. This mixture was stirred under a nitrogen atmosphere for 7.5 hours while heating at 90° C. After the termination of the reaction, about 500 mL of hot toluene was added to the suspension and this suspension was filtered through florisil, alumina, and Celite®. The obtained filtrate was concentrated, and its residue is mixed with hexane-ethyl acetate and irradiated with an ultrasonic wave. The obtained suspension was filtered and the residue was dried to obtain 15 g (yield: 75%) of 3-(N-phenylamino)-9-phenylcarbazole which was cream-colored powder. NMR data are shown below. 1H-NMR (300 MHz, CDCl3): δ=6.84 (t, J=6.9, 1H), 6.97 (d, J=7.8, 2H), 7.20-7.61 (m, 13H), 7.90 (s, 1H), 8.04 (d, J=7.8, 1H). A 1H-NMR chart is shown in FIG. 25, and an enlarged view of a portion of 5.0 ppm to 9.0 ppm in FIG. 25 is shown in FIG. 26.

Provenance & Evidence