Hydrochloric Acid → HCID 22934100, compound

HRID 1269847Notes

Reaction equation

HRID 1269847 reaction equation
[OH-].[Na+].C([N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]=[N:7]1)(=O)C.Cl>CO.O1CCCC1.O>[CH3:16][O:15][C:11]1[C:10]([C:17]([F:20])([F:18])[F:19])=[C:9]2[C:14](=[CH:13][CH:12]=1)[NH:6][N:7]=[CH:8]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22933528HCID 22933528, compound

Product 1

HCID 22934100HCID 22934100, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 6N-aqueous sodium hydroxide solution (3.8 ml, 23 mmol) was added dropwise to a solution of 1-acetyl-5-methoxy-4-(trifluoromethyl)-1H-indazole (493 mg, 1.91 mmol) in a mixture of methanol (3.8 ml) and tetrahydrofuran (3.8 ml) at room temperature and stirred at room temperature for 5 hours while maintaining the temperature. The resulting reaction solution was adjusted to pH 8 to 9 by dropwise addition of 12N-aqueous hydrochloric acid solution (1.5 ml) and then a 1N aqueous hydrochloric acid solution (about 2 ml), and distilled under reduced pressure to remove the organic solvent. The white precipitate formed was diluted with water, filtered, washed with water, and then dried under reduced pressure to obtain 5-methoxy-4-(trifluoromethyl)-1H-indazole (400 mg, 97%).

Workup

  1. temperaturewhile maintaining the temperature
  2. customThe resulting reaction solution
  3. distillationa 1N aqueous hydrochloric acid solution (about 2 ml), and distilled under reduced pressure
  4. customto remove the organic solvent
  5. customThe white precipitate formed
  6. filtrationfiltered
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-338d72cc79ac424c92b560752b194a1b
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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