Ammonium Hydroxide → HCID 178505609, compound

HRID 1462642Notes

Reaction equation

HRID 1462642 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])=[N: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](=[N: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 178510699HCID 178510699, compound

Product 1

HCID 178505609HCID 178505609, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2.0 g (6.1 mmole) of 4-[2-(2-fluorobenzoyl)-4-chlorophenyl]-1H-pyrazole-3-carbonitrile, ca 2 g. of Raney nickel, and 100 ml of acetic acid was hydrogenated on a Parr apparatus for 4 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 washed with water, dried with anhydrous sodium sulfate, and concentrated at reduced pressure to give a pale yellow solid. Recrystallization from a mixture of ether and methylene chloride gave cream colored prisms, mp 208°-210°.

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. washThe methylene chloride solution was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customto give a pale yellow solid
  10. customRecrystallization
  11. additionfrom a mixture of ether and methylene chloride
  12. customgave cream colored prisms, mp 208°-210°

Sources & evidence

ORD record
ord-75aa6fb358ba48888c351379e38ab022
Source dataset
uspto-grants-1984_07
Patent number
US04460781

Reaction notes

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