23 found c 65 06 h 4 42 n 14 33 7 chloro 5 phenyl 1 2 3 4 tetrahydro 2 nitromethylene 5h 1 5 benzodiazepin 4 one 18 3 g 055 mole was dissolved in 300 ml of dimethylformamide by gentle heating on a steam bath the solution was cooled to room temperature and 400 ml of ethanol and 55 g of raney nickel were added the mixture was hydrogenated at atmospheric pressure for 21 hours the catalyst was filtered off and washed well with tetrahydrofuran and methylene chloride the filtrate was evaporated and the residue was dissolved in 325 ml of xylene and 40 ml of triethyl orthoacetate was added to the solution which was then refluxed for 1 hour the mixture was evaporated and the residue was crystallized from ethyl acetate to yield end product with mp 248 u00b0 251 u00b0 the analytical sample was recrystallized from methylene chloride ethyl acetate to give colorless crystals with mp 250 252 anal calcd for c 18 h 16 n 3 ocl c 66 36 h 4 95 n 12 90 found c 66 11 h 4 94 n 12 98 a mixture of 7 2 g 0 022 moles of 8 chloro 1 methyl 6 phenyl 3 3a 4 6 tetrahydro 5h imidazo 1 5 a 1 5 benzodiazepin 5 one 45 g of activated manganese.