Water → Ethyl 2-oxo-2,3-dihydro-1H-indole-6-carboxylate

HRID 555664Notes

Reaction equation

HRID 555664 reaction equation
[C:1]([CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][C:6]=1[N+:16]([O-])=O)(O)=[O:2].[H][H].O>C(O)(=O)C.[C].[Pd]>[O:2]=[C:1]1[CH2:4][C:5]2[C:6](=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=2)[NH:16]1

Participants

6

Reactant 3

HCID 962WaterHCID 44190175HCID 44190175, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22567483Ethyl 2-oxo-2,3-dihydro-1H-indole-6-carboxylate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

4 g (15.8 mmol) of the thus obtained ethyl 4-(carboxymethyl)-3-nitrobenzoate and 0.45 g of 10% palladium-carbon were suspended in 15 mL of acetic acid, and the resulting mixture was stirred at room temperature in a hydrogen gas atmosphere for 23 hours. After completion of the reaction, water was added to the reaction mixture and the mixture was filtered to remove insoluble matter, and the filtrate was subjected to extraction with chloroform. The obtained chloroform layer was evaporated to dryness under reduced pressure, and water was added to the residue. Precipitated ethyl 2-oxoindoline-6-carboxylate was then obtained by filtration.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationthe mixture was filtered
  3. customto remove insoluble matter
  4. extractionthe filtrate was subjected to extraction with chloroform
  5. customThe obtained chloroform layer was evaporated to dryness under reduced pressure, and water
  6. additionwas added to the residue

Sources & evidence

ORD record
ord-5706eecd83bc4db4a03e90d0ce16fd15
Source dataset
uspto-grants-2011_11
Patent number
US08053461B2

Reaction notes

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