ACID-HYDROLYSIS OF DIAZEPAM - KINETIC-STUDY OF THE REACTIONS OF 2-(N-METHYLAMINO)-5-CHLOROBENZOPHENONE, WITH HCL IN MEOH-H2O

In the acid hydrolysis of diazepam (1), several unusual products, apar t from 2-(N-methylamino)-5-chlorobenzophenone (21 and glycine, were is olated. On the assumption that some of those products could arise from further degradation of 2, the reaction of this compound with 0.5-2 M HCl was studied, in 1:1 MeOH-H2O, at 60 and 80 degrees C. Several unex pected products were isolated from the reaction of 2 with HCl, namely, 2-amino-5-chlorobenzophenone (3), 2-(N,N-dimethylamino)5-chlorobenzop henone (4), 2-(N-methylamino)-3,5-dichlorobenzophenone (5), 2-amino-3, 5-dichlorobenzophenone (6), 2,4-dichloro-10-methyl-9,10-acridinone (7) , and 2,4-dichloro-9,10-acridinone (8). The methyl transfers, the chlo rination, and the cyclization reactions that give rise to products 3-8 are unexpected under the present reaction conditions. The rate of rea ction of 2, as well as the rate of formation of compounds 3-8, was mea sured at several HCl concentrations.