Benzoyl Peroxide → 10,11-Dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

6.60 g (0.030 mols) of (I) are dissolved in 45 ml of chlorobenzene, heating to 50° C. under stirring, then added with 0.82 g (0.003 mols) of copper(II) benzoate and 6.9 g (0.033 mols) of dibenzoylperoxide. The reaction mixture is heated to 90° C. and stirred for 3 hours, then cooled to 40° C., added with 40 ml of a 3% HCI solution and stirred at 40° C. for 30 minutes, then at 80° C. for 5 hours. 20 ml of a NaHCO3 saturated solution are added to the mixture, which is stirred for 30 minutes and decanted for 1 hour The aqueous phase is separated and re-extracted with 8 ml of chlorobenzene. The combined organic phases are washed with water (10 ml), dried and concentrated at 60° C. to 20 ml, and 20 ml of hexane are added at this temperature. The mixture is cooled to 0-5° C. for 30 minutes and the solid is filtered to obtain 3.16 g (45%) of compound (VI), m.p. 112-3° C., with good purity.

Provenance & Evidence