2-Chloroaniline → 2-Chlorophenyl-(8,8-dimethyl-8H-indolo[3,2,1-de]acridin-3-yl)amine

Participants

Reaction Steps

66.2 g (183 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine (Br-1), 28 g (220 mmol) of 2-chlorophenylamine, 1.5 g of DPPF (2.7 mmol), 0.5 g of palladium(II) acetate and 45 g of sodium tert-butoxide (486 mmol) are heated at the boil in 1.5 l of toluene for 18 h under a protective atmosphere. The mixture is subsequently partitioned between toluene and water, and the organic phase is washed three times with water and dried over Na2SO4 and evaporated in a rotary evaporator. The residue remaining is recrystallised from heptane/ethyl acetate. The yield is 43 g (107 mmol, 59%).

Provenance & Evidence