HCID 19067760, compound → HCID 19067762, compound

HRID 1957617Notes

Reaction equation

HRID 1957617 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[C:3]=1C(=O)C1C=CC([N+]([O-])=O)=CC=1.[H][H].C([O:33][CH2:34][CH3:35])(=O)C.[CH2:36](O)[CH3:37]>[Pd]>[Cl:1][CH:2]1[CH:16]=[CH:15][C:5]2[N:6]([C:34](=[O:33])[C:35]3[CH:37]=[CH:36][C:5]([NH2:6])=[CH:4][CH:3]=3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 19067760HCID 19067760, compoundHCID 21584252Ethanol ethylacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 19067762HCID 19067762, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2.1 g of 2-chloro-1-(4-nitrobenzoyl)-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-ef2f2c39c46b410dbb0f14850b4b4fd5
Source dataset
uspto-grants-1998_07
Patent number
US05786353

Reaction notes

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