HCID 13067091, compound → HCID 13067111, compound

HRID 647624Notes

Reaction equation

HRID 647624 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 of 55 psi overnight. The catalyst was removed by filtration and the acetic acid was removed at reduced pressure. The residue was diluted with water, basififed with concentrated ammonium hydroxide 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 cyrstals (mp 219°-222°). Recrystallization from a mixture of ether and methylene chloride gave colorless crystals, mp 221°-225°.

Workup

  1. customwas hydrogenated on a Parr apparatus of 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 cyrstals (mp 219°-222°)
  11. customRecrystallization
  12. additionfrom a mixture of ether and methylene chloride
  13. customgave colorless crystals, mp 221°-225°

Sources & evidence

ORD record
ord-416a3fb2b1cf464d9bce4d7cb6d7c5bf
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

Loading…