Hydrochloric Acid → 4-fluoro-1-(propan-2-yl)-1H-pyrazole-5-carboxylic acid

HRID 244657Notes

Reaction equation

HRID 244657 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([CH:12]([CH3:14])[CH3:13])[C:6]=1[C:7]([O:9]CC)=[O:8].Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[N:4][N:5]([CH:12]([CH3:14])[CH3:13])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58356353ethyl 4-fluoro-1-(1-methylethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 583563414-fluoro-1-(propan-2-yl)-1H-pyrazole-5-carboxylic acidYield 23.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-fluoro-1-(1-methylethyl)-1H-pyrazole-5-carboxylate (100 mg) in 1,4-dioxane (2 ml) was added 2M hydrochloric acid (2 ml) and the mixture heated at reflux under nitrogen for 58 h, allowed to stand at room temperature for 62 h, then heated at reflux under Nitrogen for 72 h. The mixture was cooled to room temperature and the solvent was removed in vacuo. Toluene (15 ml) was added and the solvent removed in vacuo to give a white solid that was dried in a vacuum oven overnight to give the title compound (20 mg) as a white solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux under nitrogen for 58 h
  3. temperatureheated
  4. temperatureat reflux under Nitrogen for 72 h
  5. customthe solvent was removed in vacuo
  6. additionToluene (15 ml) was added
  7. customthe solvent removed in vacuo
  8. customto give a white solid
  9. customthat was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-6f6d183073d742b2b56c8012a9678987
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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