Acetic Anhydride → 1-Acetyl-5-fluoro-1,3-dihydro-indol-2-one

HRID 74513Notes

Reaction equation

HRID 74513 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:11])(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-one

Product 1

HCID 583867501-Acetyl-5-fluoro-1,3-dihydro-indol-2-one

Procedure

At 170° C. 3.0 g (20 mmol) 5-fluoroindolinone were stirred for 3 h in 10 mL (98 mmol) acetic anhydride. After cooling to RT the mixture was poured onto 200 mL ice water, the precipitated substance was suction filtered and washed with 100 mL water. The solid was recrystallised from 100 mL water and 50 mL ethanol at boiling temperature. The precipitated product was suction filtered, washed with 30 mL water and dried in the CAD.

Workup

  1. customAt 170° C
  2. filtrationfiltered
  3. washwashed with 100 mL water
  4. customThe solid was recrystallised from 100 mL water and 50 mL ethanol
  5. filtrationfiltered
  6. washwashed with 30 mL water
  7. customdried in the CAD

Sources & evidence

ORD record
ord-5e3192e3dfd249f69143016f8f40d71d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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