Hydrochloric Acid → 2-(1H-indazol-5-yloxy)benzoic acid

HRID 1269853Notes

Reaction equation

HRID 1269853 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([O:15]C)=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+].Cl>O1CCCC1.CO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([OH:15])=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22933647HCID 22933647, compound

Product 1

HCID 229333592-(1H-indazol-5-yloxy)benzoic acidYield 86.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The methyl 2-(1H-indazol-5-yloxy)benzoate (960 mg, 3.58 mmol) synthesized in Example 478 was dissolved in a mixture of tetrahydrofuran (10 ml) and methanol (5 ml), and a 1N-aqueous sodium hydroxide solution (7 ml) was added thereto at room temperature and then stirred at 60° C. for 40 minutes. After the reaction, the reaction solution was cooled to 0° C., adjusted to pH 4 with a 2N-aqueous hydrochloric acid solution, and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain 2-(1H-indazol-5-yloxy)benzoic acid (790 mg, 86%).

Workup

  1. customAfter the reaction
  2. temperaturethe reaction solution was cooled to 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9980f99406854940a58499e5c3709624
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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