Acetic Acid → 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid

HRID 1019158Notes

Reaction equation

HRID 1019158 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].CCCCCC.C(O)(=O)C>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

5

Reactant 3

HCID 176Acetic AcidHCID 8058HexaneHCID 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 and refluxed for 2 hours with 1.1 g of tin (11) chloride in 20 mL of ethanol. The mixture was filtered through Celite, concentrated and chromatographed on silica gel in ethyl acetate:hexane:acetic acid to give 0.65 g (37% yield) of 4-carboxy-2-oxindole as a while solid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. temperaturerefluxed for 2 hours with 1.1 g of tin (11) chloride in 20 mL of ethanol
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated
  5. customchromatographed on silica gel in ethyl acetate

Sources & evidence

ORD record
ord-d014433bbe484b25a3e907722e224996
Source dataset
uspto-grants-2002_11
Patent number
US06486185B1

Reaction notes

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