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Hydrochloric Acid → 1-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylic acid

HRID 511837
Notes
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Reaction equation

HRID 511837 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[C:4]([C:15]([O:17]C)=[O:16])=[N:3]1.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:13])([F:14])[F:12])[CH:9]=2)[C:4]([C:15]([OH:17])=[O:16])=[N:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67291403methyl 1-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylate

Product 1

HCID 672898441-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a tetrahydrofuran (2 mL) of methyl 1-methyl-6-(trifluoromethyl)-1H-indazole-3-carboxylate (50 mg, 0.19 mmol) was added 2N sodium hydroxide (0.2 ml, 4.0 mmol) at room temperature. The mixture was refluxed at 90° C. with stirring for 3 hours. After being cooled to room temperature, 2N hydrochloric acid was added to the mixture until pH became 4.0. The organic layer was extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. After the filtration to separate solvent and magnesium sulfate, the solvent was removed under reduced pressure to give 47 mg (quantitative yield) of the title as a white solid that was used in the next step without further purification;

Workup

  1. temperatureAfter being cooled to room temperature
  2. extractionThe organic layer was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter the filtration
  6. customto separate solvent and magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto give 47 mg (quantitative yield) of the title as a white solid that
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6579fd8e7f644ad7aa00b6a1c1a42870
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09101616B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes