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

HRID 2080558Notes

Reaction equation

HRID 2080558 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>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

5

Reactant 2

HCID 14797Potassium HydroxideHCID 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 Example 4) (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 hexanes-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

Sources & evidence

ORD record
ord-19bbbf37379444a29886feeacab150fc
Source dataset
uspto-grants-2011_04
Patent number
US07932395B2

Reaction notes

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