Hydrochloric Acid → 1-ethyl-4-fluoro-1H-pyrazole-5-carboxylic acid

HRID 244661Notes

Reaction equation

HRID 244661 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([F:13])[CH:5]=[N:4]1)[CH3:2].Cl>O1CCOCC1>[CH2:1]([N:3]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58356399ethyl 1-ethyl-4-fluoro-1H-pyrazole-5-carboxylate

Product 1

HCID 583564401-ethyl-4-fluoro-1H-pyrazole-5-carboxylic acidYield 45.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 1-ethyl-4-fluoro-1H-pyrazole-5-carboxylate (67 mg) in 1,4-dioxane (3 ml) was added 2M hydrochloric acid (2 ml) was added and the mixture was heated at reflux under nitrogen for 120 h. The mixture was cooled to room temperature and the solvent was removed in vacuo. Toluene (15 ml) was added and the solvent was removed in vacuo to give a solid that was dried in a vacuum oven overnight to give the title compound (26 mg) as a brown solid.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux under nitrogen for 120 h
  4. customthe solvent was removed in vacuo
  5. additionToluene (15 ml) was added
  6. customthe solvent was removed in vacuo
  7. customto give a solid
  8. customthat was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-11e4c56967834f96826b35e474adafa2
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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