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

HRID 1938212Notes

Reaction equation

HRID 1938212 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH2:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)=[O:9])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 544990776,11Dihydro-5-(4-nitrobenzoyl)-5H-dibenz[b,e]azepine

Product 1

HCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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 (Na2 SO4). 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. Anal. Calc'd for C21 H18N2O: C,80.2; H,5.8; N,8.9. Found: C,79.2; H,6.0; N,8.8.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-bafbd3e466e241129eba5b3216294c96
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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