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

HRID 858295Notes

Reaction equation

HRID 858295 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 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, the solvent distilled off. The crude product is stirred with 500 ml petroleum ether, suction filtered, washed with water and dried.

Workup

  1. filtrationfiltered
  2. distillationthe solvent distilled off
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-50accfa8a926434eb75cd21f6a211fbe
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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