Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate → 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid

HRID 2101546Notes

Reaction equation

HRID 2101546 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[CH:14](C(OC)=O)[C:15]([O:17]C)=O)=[O:4]>Cl>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[CH2:14][C:15](=[O:17])[NH:11]2)([OH:2])=[O:4]

Participants

3

Reactant 1

HCID 54355276Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

Product 1

HCID 103973292-oxo-2,3-dihydro-1H-indole-4-carboxylic acidYield 38.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate (3.0 g) was refluxed in 50 mL of 6 N hydrochloric acid overnight. The mixture was concentrated to dryness, 20 mL ethanol and 1.1 g of tin(II) chloride were added and the mixture was refluxed for 2 hours. The mixture was filtered through Celite, concentrated and chromatographed on silica gel using ethyl acetate:hexane:acetic acid as eluent to give 0.65 g (37%) of 4-carboxy-2-oxindole as a white solid.

Workup

  1. concentrationThe mixture was concentrated to dryness, 20 mL ethanol and 1.1 g of tin(II) chloride
  2. additionwere added
  3. temperaturethe mixture was refluxed for 2 hours
  4. filtrationThe mixture was filtered through Celite
  5. concentrationconcentrated
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-3fc27ed7e09046948064739e57aa3c7b
Source dataset
uspto-grants-2009_08
Patent number
US07572924B2

Reaction notes

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