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

HRID 1985870Notes

Reaction equation

HRID 1985870 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>[Pd].C(O)(=O)C>[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

4

Reactant 1

HCID 107504922-(4-Fluoro-2-nitrophenyl)acetic acid2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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

Workup

  1. filtrationThe catalyst is filtered off with suction
  2. distillationthe solvent is distilled off
  3. customThe crude product is triturated with 500 ml of petroleum ether
  4. filtrationfiltered off with suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-83cf3393604b4cd99a06f604ee1f9924
Source dataset
uspto-grants-2009_06
Patent number
US07547703B2

Reaction notes

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