Nitrogen → 2-Chloro-9,9-dimethyl-10-phenyl-9,10-dihydroacridine

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Reaction Steps

A degassed solution of 16.6 ml (147 mmol) of 4-iodobenzene and 30 g (123 mmol) of 2-chloro-9,9-dimethyl-9,10-dihydroacridine in 600 ml of toluene is saturated with N2 for 1 h. Then firstly 2.09 ml (8.6 mmol) of P(tBu)3 and then 1.38 g (6.1 mmol) of palladium(II) acetate are added to the solution. 17.7 g (185 mmol) of NaOtBu as solid are subsequently added. The reaction mixture is heated under reflux for 1 h. After cooling to room temperature, 500 ml of water are carefully added. The aqueous phase is washed with 3×50 ml of toluene and dried over MgSO4, and the solvent is removed in vacuo. Filtration of the crude product through silica gel with heptane/ethyl acetate (20:1) gives 32.2 g (81%) of 2-chloro-9,9-dimethyl-10-phenyl-9,10-dihydroacridine as pale-yellow crystals.

Provenance & Evidence