Thionyl Chloride → 4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzonitrile

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Reaction Steps

A solution of 4-cyano-3-methylbenzoic acid from Example C (1.2 g, 7.5 mmol) and thionyl chloride (3.6 ml, 54 mmol) in toluene (20 ml) was heated at reflux for 2 h. The mixture was evaporated and azeotroped with toluene. The residue was dissolved in dichloromethane, 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine (1.4 g, 7.5 mmol) was added and the mixture stirred for 18 h. The mixture was evaporated and the residue purified by flash chromatography on silica (EtOAc:pet ether, 30:70 to 80:20) to give a cream solid, yield 1.5 g, 63%.

Provenance & Evidence