Ammonium Hydroxide → HCID 136045442, compound

HRID 2296270Notes

Reaction equation

HRID 2296270 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:14]([C:18]#[N:19])=[CH:15][NH:16][CH:17]=1)=O.[OH-].[NH4+]>[Ni].C(O)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]2[C:13]3[C:14](=[CH:15][NH:16][CH:17]=3)[CH2:18][N:19]=[C:4]([C:3]3[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=3[F:1])[C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 130670874-[4-Chloro-2-(2-fluorobenzoyl)phenyl]-1H-pyrrole-3-carbonitrile

Product 1

HCID 136045442HCID 136045442, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3.0 g (9 mmole) of 4-[2-(2-fluorobenzoyl)-4-chlorophenyl]-1H-pyrrole-3-carbonitrile, ca 3 g of Raney nickel and 150 ml of glacial acetic acid was hydrogenated on a Parr apparatus at 50 psi for 6 hr. The Raney nickel was removed by filtration, and the acetic acid was removed at reduced pressure to give a yellow oil. The yellow oil was poured over ice, basified with ammonium hydroxide and extracted with methylene chloride. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give tan crystals. Recrystallization from a mixture of ether and methylene chloride gave cream prisms, mp 197°-199°.

Workup

  1. customThe Raney nickel was removed by filtration
  2. customthe acetic acid was removed at reduced pressure
  3. customto give a yellow oil
  4. additionThe yellow oil was poured over ice
  5. extractionextracted with methylene chloride
  6. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customto give tan crystals
  9. customRecrystallization
  10. additionfrom a mixture of ether and methylene chloride
  11. customgave cream prisms, mp 197°-199°

Sources & evidence

ORD record
ord-8b77da158c9a4906969810a2aea593fa
Source dataset
uspto-grants-1984_01
Patent number
US04428878

Reaction notes

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