HCID 13067091, compound → HCID 13067111, compound

HRID 1903626Notes

Reaction equation

HRID 1903626 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][NH:11][C:12]=2[CH3:13])=[C:4]([C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH:3]=1>[Ni].C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[CH:10][NH:11][C:12]=3[CH3:13])[CH2:14][N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 13067091HCID 13067091, compound

Product 1

HCID 13067111HCID 13067111, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8.5 g (24 mmol) of 4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1H-pyrrole-3-carbonitrile, 1 spoonful of Raney nickel and 250 ml of glacial acetic acid was hydrogenated on a Parr apparatus at 55 psi overnight. The catalyst was removed by filtration, and the acetic acid was removed at reduced pressure. The residue was diluted with water, basified with concentrated ammonium hydroxide solution, and the resulting precipitate was collected by filtration. The precipitate was dissolved in tetrahydrofuran, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was crystallized from a mixture of ether and petroleum ether to give off-white crystals, mp 219°-222° C. Recrystallization from a mixture of ether and methylene chloride gave colorless crystals, mp 221°-225° C.

Workup

  1. customwas hydrogenated on a Parr apparatus at 55 psi overnight
  2. customThe catalyst was removed by filtration
  3. customthe acetic acid was removed at reduced pressure
  4. additionThe residue was diluted with water
  5. filtrationthe resulting precipitate was collected by filtration
  6. dissolutionThe precipitate was dissolved in tetrahydrofuran
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was crystallized from a mixture of ether and petroleum ether
  10. customto give off-white crystals, mp 219°-222° C
  11. customRecrystallization
  12. additionfrom a mixture of ether and methylene chloride
  13. customgave colorless crystals, mp 221°-225° C.

Sources & evidence

ORD record
ord-488e555c70784982bd13fef9d201c676
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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