Acetic Acid → 3-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic Acid

HRID 503112Notes

Reaction equation

HRID 503112 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=C(C#N)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:24]([OH:27])(=[O:26])[CH3:25]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:25]([C:24]([OH:27])=[O:26])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 222606703-(4-Fluorophenyl)-1H-indazole-5-carbonitrile

Product 1

HCID 222607223-(4-Fluorophenyl)-1H-Indazole-5-Carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 1.0 g of 3-(4-fluorophenyl)-1H-5-indazolecarbonitrile were added 5 ml of water, 4 ml of concentrated sulfuric acid and 4 ml of glacial acetic acid, and the mixture was heated under reflux for 3 hours. After standing to cool, 25 ml of ice-cooled water was added. The resulting crystals were collected by filtration. The collected crystals were dissolved in 250 ml of ethyl acetate, sequentially washed with water and brine, and dried over anhydrous magnesium sulfate. After filtrating the organic layer through a silica gel pat, the solvent was evaporated, to give 968 mg of the title compound as bright yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. additionwas added
  5. filtrationThe resulting crystals were collected by filtration
  6. dissolutionThe collected crystals were dissolved in 250 ml of ethyl acetate
  7. washsequentially washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtrating the organic layer through a silica gel pat
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bac381b6a5eb4f46a79ee606324cf4a5
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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