Sodium Hydroxide → HCID 178524803, compound

HRID 1750424Notes

Reaction equation

HRID 1750424 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178469915HCID 178469915, compound

Product 1

HCID 178524803HCID 178524803, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (25.0 g, 107 mmol) obtained in step 2 in ethanol (90 mL) was added 2N aqueous sodium hydroxide solution (117 mL, 235 mmol) at room temperature, and the mixture was heated under reflux for 24 hr. The organic solvent was evaporated, and ethyl acetate was added to the residue. The aqueous layer was separated, and 2N hydrochloric acid was added until the aqueous layer became pH2. The precipitate was collected by filtration to give 3-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid (22.8 g, 100%) as a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. customThe organic solvent was evaporated
  4. additionethyl acetate was added to the residue
  5. customThe aqueous layer was separated
  6. addition2N hydrochloric acid was added until the aqueous layer
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b477207b7ab24fc08b9c69413b064667
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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