HCID 178510698, compound → HCID 178477843, compound

HRID 1462636Notes

Reaction equation

HRID 1462636 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-5051eb0c44e9428a8b57ff6d837abdcd
Source dataset
uspto-grants-1984_07
Patent number
US04460781

Reaction notes

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