4-Methoxy-2-indolinone → 4-Hydroxyindolin-2-one

HRID 1634722Notes

Reaction equation

HRID 1634722 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:12])[NH:7]2.[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:12])[NH:7]2

Participants

3

Reactant 2

HCID 5960014-Methoxy-2-indolinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5909114-Hydroxyindolin-2-oneYield 94%

Conditions

Temperature
235 °C

Procedure

A mixture of 4-methoxy-2-oxindole (3.5 g, 21.4 mmol) and 3.0 g of aluminum chloride was heated at 235° C. for 10 minutes with stirring. On cooling the sludge was triturated with H2O. The solids were filtered washed with H2O and dried to give 3.0 g of product as an orange solid. Purified by flash chromatography (hexane-ethyl acetate 3:1) to give 1.1 g of pure title compound.

Workup

  1. temperatureOn cooling the sludge
  2. customwas triturated with H2O
  3. filtrationThe solids were filtered
  4. washwashed with H2O
  5. customdried

Sources & evidence

ORD record
ord-c63c89bc539440fc85cea088256e408b
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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