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

HRID 1057431Notes

Reaction equation

HRID 1057431 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 was heated to refulux in 50 mL of 6 N hydrochloric acid overnight. The mixture was concentrated to dryness and was heated to refulux for 2 hours with 1.1 g of tin(II) 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 white solid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. temperaturewas heated
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated
  5. customchromatographed on silica gel in ethyl acetate

Sources & evidence

ORD record
ord-9901b7b07ced4d9d9b8e810e4e260a99
Source dataset
uspto-grants-2003_02
Patent number
US06514981B1

Reaction notes

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