Potassium Hydroxide → HCID 19080749, compound

HRID 963148Notes

Reaction equation

HRID 963148 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[CH:13]=[O:14].[OH-].[K+].[Mn]([O-])(=O)(=O)=[O:18].[K+]>O.ClCCl>[Cl:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[C:4]([C:9]([F:10])([F:12])[F:11])[C:3]=1[C:13]([OH:18])=[O:14]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 19080746HCID 19080746, compound

Product 1

HCID 19080749HCID 19080749, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 29.5 g (131 mmol) of 5-chloro-1-ethyl-3-(trifluoromethyl)-pyrazole-4-carboxaldehyde in 350 mL of distilled water was prepared and 0.733 g (131 mmol) of potassium hydroxide and 20.6 g (131 mmol) of potassium permanganate were added to it. The mixture was heated to 60° C. with stirring for 2 hours. The color turned from purple to dark brown. An aliquot was taken, filtered to remove the solids, acidified, and analyzed by gas chromatography to determine that the reaction was complete. The reaction mixture was then filtered to remove the solids and the filtrate was acidified to pH 2. The precipitate that formed was recovered by filtration and washed with water to obtain a white solid. This solid was partially dissolved in hot dichloromethane and the insoluble portion removed by gravity fIltration. The filtrate was concentrated by evaporation under reduced pressure to obtain 23.4 g of the title compound as a white solid melting at 164°-166° C.

Workup

  1. customwas prepared
  2. filtrationfiltered
  3. customto remove the solids
  4. filtrationThe reaction mixture was then filtered
  5. customto remove the solids
  6. customThe precipitate that formed
  7. filtrationwas recovered by filtration
  8. washwashed with water
  9. customto obtain a white solid
  10. customthe insoluble portion removed by gravity fIltration
  11. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-01acbcdf84394203b5395d6ff9a3f4a5
Source dataset
uspto-grants-1998_06
Patent number
US05763359

Reaction notes

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