(3-Fluoro-2-nitrophenyl)acetic acid → 7-Fluoro-2,3-dihydro-1h-indol-2-one

HRID 2250517Notes

Reaction equation

HRID 2250517 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:12][C:9](=[O:10])[CH2:8]2

Participants

4

Reactant 1

HCID 24824213(3-Fluoro-2-nitrophenyl)acetic acid

Product 1

HCID 37343717-Fluoro-2,3-dihydro-1h-indol-2-oneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(3-fluoro-2-nitro-phenyl)-acetic acid (9.6 g, 48 mmol) was dissolved in acetic acid (100 mL) and hydrogenated over 10% palladium on carbon (1.3 g), at 50 psi for 24 hours. The catalyst was removed by filtration through the Celite® reagent and the solvent was evaporated. The mixture was then dissolved in ethanol (100 mL), para-toluenesulfonic acid (50 mg) was added and the mixture heated under reflux for 1 hour. The mixture was cooled, poured into water, extracted with ethyl acetate, dried (MgSO4), and evaporated. The solid was triturated with hexane/ethyl acetate (95/5) to give 7-fluoro-1,3-dihydro-indol-2-one (6 g, 83%). HRMS: calc'd for C8H6FNO, 151.0433; found (ESI, [M+H]+), 152.0515

Workup

  1. customThe catalyst was removed by filtration through the Celite® reagent
  2. customthe solvent was evaporated
  3. dissolutionThe mixture was then dissolved in ethanol (100 mL)
  4. additionpara-toluenesulfonic acid (50 mg) was added
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 1 hour
  7. temperatureThe mixture was cooled
  8. additionpoured into water
  9. extractionextracted with ethyl acetate
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe solid was triturated with hexane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-4f2876eb72624720885d110d9afe8876
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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