2-(4-Fluoro-2-nitrophenyl)acetic acid → 6-fluoro-2,3-dihydro-1H-indol-2-one

HRID 2109013Notes

Reaction equation

HRID 2109013 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=[O:10])=[C:4]([N+:12]([O-])=O)[CH:3]=1.[H][H]>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][C:9](=[O:10])[NH:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 107504922-(4-Fluoro-2-nitrophenyl)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 37310136-fluoro-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

119 g 4-fluoro-2-nitrophenylacetic acid (educt III) are hydrogenated in 600 ml acetic acid with the addition of 20 g palladium on activated charcoal (10%) under 50 psi of hydrogen pressure. The catalyst is suction filtered and the solvent is distilled off. The crude product is extracted with 500 ml petroleum ether, suction filtered, washed with water and dried.

Workup

  1. filtrationfiltered
  2. distillationthe solvent is distilled off
  3. extractionThe crude product is extracted with 500 ml petroleum ether, suction
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-839aa1031bec4dc98dfc13ed1fd21d73
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

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