6,11Dihydro-5-(4-nitrobenzoyl)-5H-dibenz[b,e]azepine → 5-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

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Reaction Steps

To a solution of 4.5 g of 6,11-dihydro-5-(4-nitrobenzoyl)-5H-dibenz[b,e]azepine in 230 ml of glacial acetic acid is added 0.58 g of 10% palladium-on-carbon and the mixture under hydrogen (38 psi) shaken in a Parr hydrogenator for 6.5 hours. The mixture is filtered through diatomaceous earth and the filtrate concentrated to give 4.0 g of solid. The solid is extracted with 100 ml of dichloromethane and the extract washed with water, dried (Na2SO4). The solvent is removed to give 4.0 g of yellow crystals, m.p. 168°-175° C. A sample chromatographed on a thick layer silica gel plate with hexane-ethyl acetate (8:7) as solvent gives yellow crystals, m.p. 173°-175° C.

Provenance & Evidence