Ammonium Hydroxide → HCID 136045442, compound

HRID 1903623Notes

Reaction equation

HRID 1903623 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 mmol) 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 hours. 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 on to ice, basified with ammonium hydroxide solution 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-colored prisms, mp 197°-199° C.

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 on to 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-colored prisms, mp 197°-199° C.

Sources & evidence

ORD record
ord-faa2c672de604aebb9e58eea5306c9da
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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