HCID 19899911, compound → 4-Fluoro-1,3-dihydro-2H-indol-2-one

HRID 2250521Notes

Reaction equation

HRID 2250521 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][C:12]([OH:14])=O>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:11][C:12](=[O:14])[NH:8]2

Participants

4

Reactant 1

HCID 19899911HCID 19899911, compound

Product 1

HCID 155125994-Fluoro-1,3-dihydro-2H-indol-2-oneYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(2-fluoro-6-nitrophenyl)acetic acid (3.3 g, 16.6 mmol) was dissolved in acetic acid (20 mL) and hydrogenated over palladium on carbon (10%, 0.5 g) at 50 psi for 24 hours. The catalyst was removed by filtration through the Celite® reagent, which was washed with methanol, and the combined organics were then evaporated. The reaction mixture was then dissolved in ethanol (100 mL), 50 mg of para-toluenesulfonic acid was added, and the mixture heated under reflux for 1 hour. The mixture was poured into water, extracted with ethyl acetate, dried over magnesium sulfate, and evaporated. The solid was triturated with hexane/ethyl acetate (95/5) to give 1.7 g, 67% of 4-fluoro-1,3-dihydro-2H-indol-2-one: HRMS [M+H]+=152.0515

Workup

  1. customThe catalyst was removed by filtration through the Celite® reagent, which
  2. washwas washed with methanol
  3. customthe combined organics were then evaporated
  4. dissolutionThe reaction mixture was then dissolved in ethanol (100 mL)
  5. addition50 mg of para-toluenesulfonic acid was added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 1 hour
  8. additionThe mixture was poured into water
  9. extractionextracted with ethyl acetate
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customThe solid was triturated with hexane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-1586044487af470bb86a71d74ec3a32f
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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