Acetic Anhydride → HCID 69431575, compound

HRID 1269923Notes

Reaction equation

HRID 1269923 reaction equation
C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:13](OCCC(C)C)=O.[C:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[C:27]([CH3:35])[C:26]=1[F:36])(=[O:23])[CH3:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:21]([O:24][C:25]1[C:26]([F:36])=[C:27]2[C:28](=[CH:29][CH:30]=1)[N:31]([C:32](=[O:34])[CH3:33])[N:13]=[CH:35]2)(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 69432694HCID 69432694, compound

Product 1

HCID 69431575HCID 69431575, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (2.83 ml, 30.0 mmol), tetrabutylammonium bromide (161 mg, 0.500 mmol), potassium acetate (1.96 g, 20.0 mmol) and isoamyl nitrite (1.75 ml, 13.0 mmol) were added in that order to a solution of 4-(acetylamino)-2-fluoro-3-methylphenyl acetate (2.25 g, 9.99 mmol) in ethyl acetate (30 ml) at room temperature. The resulting mixture was slowly heated until heating under reflux was caused. Then, the mixture was stirred for 11 hours while maintaining the temperature. After cooling, the mixture was partitioned and extracted with water and ethyl acetate, and the organic phase 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: hexane/ethyl acetate) to obtain 1-acetyl-4-fluoro-1H-indazol-5-yl acetate (1.00 g, 38%).

Workup

  1. temperatureThe resulting mixture was slowly heated
  2. temperatureuntil heating
  3. temperatureunder reflux
  4. temperaturewhile maintaining the temperature
  5. temperatureAfter cooling
  6. customthe mixture was partitioned
  7. extractionextracted with water and ethyl acetate
  8. washthe organic phase was washed with an aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1b9f5fed5266411d9686ff37f3f2fe2a
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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