Hydrochloric Acid → HCID 22933665, compound

HRID 1269924Notes

Reaction equation

HRID 1269924 reaction equation
[OH-].[Na+].C([O:6][C:7]1[C:8]([F:19])=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(=O)C)[N:11]=[CH:10]2)(=O)C.O1CCCC1.Cl>CO>[F:19][C:8]1[C:7]([OH:6])=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69431575HCID 69431575, compound

Product 1

HCID 22933665HCID 22933665, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 6N aqueous sodium hydroxide solution (5 ml, 30 mmol) was added dropwise to a solution of 1-acetyl-4-fluoro-1H-indazol-5-yl acetate (995 mg, 3.78 mmol) in methanol (5 ml)-tetrahydrofuran (5 ml) at room temperature, and the resulting mixture was stirred for 3.5 hours while being maintained at room temperature. The resulting reaction solution was adjusted to pH 5 to 6 by dropwise addition of a 1N aqueous hydrochloric acid solution (about 25 ml) and extracted with ethyl acetate, and the organic layer was washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain 4-fluoro-1H-indazol-5-ol (219 mg, 38%).

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with an aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-8bb987ffb1a74cfd9fb0ee2a320d8a29
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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