2-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-phenylacetamide → 2-(3-amino-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

Zinc powder (9.1 g) was added in portions to a slurry of 2-[2,4-dioxo-5-phenyl-3-(phenylhydrazono)-2,3,4,5-tetrahydro benzo[b][1,4]-diazepin-1-yl]-N-isopropyl-N-phenylacetamide (7.5 g), in glacial acetic acid, cooled to 0° C. The reaction was allowed to warm to R.T. and stirred an additional hour. The zinc was filtered through a celite pad and the glacial acetic acid was evaporated in vacuo. The residue was dissolved in ethyl acetate (200 ml) and washed with 10% aqueous sodium carbonate (2×100 ml) and water (2×100 ml), dried (Na2SO4) and evaporated to a tan oil. Trituration with hexane and ethyl acetate provided the title compound as a light tan powder (6.3 g). 1H-NMR (300 MHz, CDCl3): d 7.6-6.8 (m, 14H), 5.05 (m, 1H), 4.3-4.0 (m, 3H) 1.05 (d, 6H); MS (FAB)=448 (MH+); TLC, Rf =0.25 (chloroform:methanol, 9:1).

Provenance & Evidence