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

HRID 2296302Notes

Reaction equation

HRID 2296302 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 mmole) 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 hr. 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 methylene chloride. The methylene chloride solution was washed with water, and was dried with sodium sulfate. Concentration of the methylene chloride solution gave a yellow solid. Recrystallization from methylene chloride/ether gave a white solid, mp 203°-206°.

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 methylene chloride
  4. washThe methylene chloride solution was washed with water
  5. dry with materialwas dried with sodium sulfate
  6. customConcentration of the methylene chloride solution gave a yellow solid
  7. customRecrystallization from methylene chloride/ether
  8. customgave a white solid, mp 203°-206°

Sources & evidence

ORD record
ord-89f5de9d962740998a47646b5180c775
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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