4-(2-Benzoyl-4-chlorophenyl)-1H-pyrrole-3-carbonitrile → 8-Chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine

HRID 1903619Notes

Reaction equation

HRID 1903619 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[C:17]([C:21]#[N:22])=[CH:18][NH:19][CH:20]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].C(O)(=O)C>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]2[C:16]3[C:17](=[CH:18][NH:19][CH:20]=3)[CH2:21][N:22]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9]=2[CH:14]=1

Participants

4

Reactant 1

HCID 130670864-(2-Benzoyl-4-chlorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 1360876848-Chloro-6-phenyl-2H,4H-pyrrolo[3,4-d][2]benzazepine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4.0 g (13 mmol) of 4-[2-benzoyl-4-chlorophenyl]-1H-pyrrole-3-carbonitrile, 4 g of Raney nickel, and 300 ml of acetic acid were hydrogenated on a Parr apparatus for 4 hours. The Raney nickel was removed by filtration, and the filtrate was diluted with 400 ml of ice water. The acetic acid was neutralized with sodium bicarbonate, and the resulting solution extracted with methyene chloride. The methylene chloride solution was washed with water and dried over sodium sulfate. Concentration of the methylene chloride solution gave a yellow solid. Recrystallization from methylene chloride/ether gave end product as white solid, mp 203°-206° C.

Workup

  1. customThe Raney nickel was removed by filtration
  2. additionthe filtrate was diluted with 400 ml of ice water
  3. extractionthe resulting solution extracted with methyene chloride
  4. washThe methylene chloride solution was washed with water
  5. dry with materialdried over sodium sulfate
  6. customConcentration of the methylene chloride solution gave a yellow solid
  7. customRecrystallization from methylene chloride/ether
  8. customgave end product as white solid, mp 203°-206° C.

Sources & evidence

ORD record
ord-c7d21245ea834deaad10a8f9a2393969
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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