HCID 10038811, compound → Methyl 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

HRID 1392256Notes

Reaction equation

HRID 1392256 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9](OC)=[O:10])[CH:7]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:17][C:9](=[O:10])[CH:8]2[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 10038811HCID 10038811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22476319Methyl 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylateYield 118.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
42.5 °C

Procedure

In a flask made of glass equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet tube and having an inner volume of 500 ml were charged 60.0 g (0.22 mol) of dimethyl 2-(5-fluoro-2-nitrophenyl)malonate synthesized according to Example 1 with a purity of 98% and 228 g of methanol under argon atmosphere. Under stirring, while maintaining the temperature of the mixture to 40 to 45° C., 3.0 g (0.72 mmol in terms of the palladium atom) of 5% by weight palladium/carbon (49% hydrated product) was added to the mixture. Then, while blowing hydrogen with a flow rate of 123 ml/min. and a normal pressure, the mixture was reacted at the same temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered to remove the catalyst, the filtrate was concentrated under reduced pressure, and 80 ml of methanol and 240 ml of water were added to the resulting concentrate and cooled to 10° C. Then, after filtration of the precipitated crystals, they were dried to obtain 54.5 g (isolation yield: 94%) of 5-fluoro-3-methoxycarbonyloxindole as white crude crystals with a purity of 80% (analytical value by high performance liquid chromatography).

Workup

  1. customIn a flask made of glass
  2. customequipped with a stirrer
  3. customsynthesized
  4. customa normal pressure, the mixture was reacted at the same temperature for 3 hours
  5. customAfter completion of the reaction
  6. filtrationthe reaction mixture was filtered
  7. customto remove the catalyst
  8. concentrationthe filtrate was concentrated under reduced pressure, and 80 ml of methanol and 240 ml of water
  9. additionwere added to the resulting
  10. concentrationconcentrate
  11. temperaturecooled to 10° C
  12. filtrationThen, after filtration of the precipitated crystals, they
  13. customwere dried

Sources & evidence

ORD record
ord-134f43f78d0d402ba8467c3e2f80c632
Source dataset
uspto-grants-2008_03
Patent number
US07342040B2

Reaction notes

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