2-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine → 2-Chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 355851Notes

Reaction equation

HRID 355851 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:15](=[O:25])[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([C:15](=[O:25])[C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 539356852-Chloro-5-(4-nitrobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineHCID 178418361HCID 178418361, compound

Product 1

HCID 544045372-Chloro-5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepineYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 2.1 g of 2-chloro-5-(4-nitro-benzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine in 400 ml of ethyl acetate-ethanol (1:1) and 0.25 g of palladium-on-carbon is hydrogenated in a Parr hydrogenator under 38 pounds per square inch of hydrogen. The mixture is filtered through diatomaceous earth and the filtrate concentrated to dryness. The solid (1.94 g) is dissolved in dichloromethane and the solution filtered through a thin pad of hydrous magnesium silicate. The filter pad is washed with dichloromethane and the filtrate concentrated. The residue is crystallized from dichloromethane-hexane to give 1.43 g of crystals, m.p. 211°-214° C.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated to dryness
  3. dissolutionThe solid (1.94 g) is dissolved in dichloromethane
  4. filtrationthe solution filtered through a thin pad of hydrous magnesium silicate
  5. washThe filter pad is washed with dichloromethane
  6. concentrationthe filtrate concentrated
  7. customThe residue is crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-f9fd24dc3152413b90d26eadbc89f6f5
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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