Quinoline → 11,12-Dihydro-11-phenylindolo[2,3-a]carbazole

Participants

Reaction Conditions

Reaction Steps

In a 1,000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 millimoles) of indolo[2,3-a]carbazole, 122.7 g (601.4 millimoles) of iodobenzene, 54.7 g (287.2 millimoles) of copper iodide, 66.7 g (482.6 millimoles) of potassium carbonate, and 800 ml of quinoline and the mixture was stirred at 190° C. for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, and the yellow crystals formed were filtered off. The filtrate was separated into an organic layer and an aqueous layer and the organic layer was washed three times with 500 ml of water. The organic layer was dried over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was stripped off under reduced pressure. The residue was purified by silica gel column chromatography to yield 13.7 g (41.2 millimoles, 40.6% yield) of 11-phenylindolo[2,3-a]carbazole as a white powder.

Provenance & Evidence