HCID 178510698, compound → HCID 178477843, compound

HRID 1701923Notes

Reaction equation

HRID 1701923 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])=[N: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](=[N: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 178510698HCID 178510698, compound

Product 1

HCID 178477843HCID 178477843, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.2 g (7.2 mmole) of 4-[2-benzoyl-4-chlorophenyl]pyrazole-3-carbonitrile, 2.0 g of Raney nickel, and 150 ml of acetic acid was hydrogenated on a Parr apparatus for 4 hr. The Raney nickel was removed by filtration, and the filtrate diluted with 600 ml of ice water. The acetic acid was neutralized with concentrated ammonium hydroxide and the resulting aqueous solution was 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 tan solid. Recrystallization from chloroform/hexane gave a white solid, mp 241°-243°.

Workup

  1. customThe Raney nickel was removed by filtration
  2. additionthe filtrate diluted with 600 ml of ice water
  3. extractionthe resulting aqueous solution was 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 tan solid
  7. customRecrystallization from chloroform/hexane
  8. customgave a white solid, mp 241°-243°

Sources & evidence

ORD record
ord-e5542efc69ca4fc9b38174f5fcd5c230
Source dataset
uspto-grants-1983_04
Patent number
US04379765

Reaction notes

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