Potassium Hydroxide → 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 516532Notes

Reaction equation

HRID 516532 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:5]([N:10]2[C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][C:12]([C:20]([F:23])([F:22])[F:21])=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1.CCCCCC.C(OCC)(=O)C>O.C(O)C>[Cl:3][C:4]1[C:5]([N:10]2[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]([C:20]([F:23])([F:21])[F:22])=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21226206Ethyl acetate hexaneHCID 22172778Ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate2×

Product 1

HCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (0.5 g, 85%, 2.28 mmol) in water (1 mL) was added to ethyl 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (i.e. the product of Step D) (0.66 g, 2.07 mmol) in ethanol (3 mL). After about 30 minutes, the solvent was removed under reduced pressure, and the mixture was dissolved in water (40 mL). The solution was washed with ethyl acetate (20 mL). The aqueous layer was acidified with concentrated hydrochloric acid and was extracted with ethyl acetate (3×20 mL). The combined extracts were dried and evaporated to give the product, as a solid (0.53 g, 93% yield), m.p. 178-179° C. (after crystallization from hexane-ethyl acetate).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe mixture was dissolved in water (40 mL)
  3. washThe solution was washed with ethyl acetate (20 mL)
  4. extractionwas extracted with ethyl acetate (3×20 mL)
  5. customThe combined extracts were dried
  6. customevaporated
  7. customto give the product

Sources & evidence

ORD record
ord-b4cf41794a0a4fa9953a53d76ac160ca
Source dataset
uspto-grants-2015_08
Patent number
US09113630B2

Reaction notes

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