ISOLATION AND STRUCTURE ELUCIDATION OF NOVEL PRODUCTS OF THE ACIDIC DEGRADATION OF DIAZEPAM

The acidic degradation of diazepam in methanolic aqueous solution has been investigated. Apart from the known degradation products, 2-(N-met hylamino)-5-chlorobenzophenone and glycine, produced by the hydrolytic cleavage of the benzodiazepinone ring, five novel products were isola ted and fully characterized by their spectroscopic features and indepe ndent synthesis. Substituted 2-amino-3,5-dichlorobenzophenones and 2,4 -dichloroacridinones were found, the formation of which in the reactio n media is mechanistically intriguing. The role of these unexpected pr oducts in accelerated studies of diazepam stability is discussed.