Hydrochloric Acid → HCID 82286168, compound

HRID 1750387Notes

Reaction equation

HRID 1750387 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]([O:16]CC)=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86721227HCID 86721227, compound

Product 1

HCID 82286168HCID 82286168, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (14.2 g, 57.4 mmol) obtained in step 1 in ethanol (50 mL) was added 2N aqueous sodium hydroxide solution (63.2 mL, 126 mmol) at room temperature, and the mixture was heated under reflux for 1 hr. The reaction mixture was cooled to room temperature, and 2N hydrochloric acid was added until the mixture became pH 6. The precipitate was collected by filtration with ethyl acetate to give a mixture (3:2.2 (mol/mol), 13.0 g, 100%) of 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carboxylic acid and 3-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. filtrationThe precipitate was collected by filtration with ethyl acetate

Sources & evidence

ORD record
ord-88b325fd888f40b5b3738ac0125c98bf
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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