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

HRID 223472Notes

Reaction equation

HRID 223472 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-5b25c75080a14a798bf0eca199d8027d
Source dataset
uspto-grants-1982_10
Patent number
US04354973

Reaction notes

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