Sulfuric Acid → 6-bromo-2,3-dihydro-1H-indol-2-one

HRID 1243470Notes

Reaction equation

HRID 1243470 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=[O:10])=[C:4]([N+:12]([O-])=O)[CH:3]=1.S(=O)(=O)(O)O>C(O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][C:9](=[O:10])[NH:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 2715514-Bromo-2-nitrophenylacetic Acid

Product 1

HCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

4-Bromo-2-nitrophenylacetic acid 0.26 g), 0.26 g zinc powder and 3 mL 50% sulfuric acid in 5 mL ethanol was heated at 100° C. overnight. The reaction mixture was filtered, diluted with a little acetic acid, concentrated to remove ethanol, diluted with water and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 0.19 g (90% yield) of 6-bromo-2-oxindole as a yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with a little acetic acid
  3. concentrationconcentrated
  4. customto remove ethanol
  5. additiondiluted with water
  6. extractionextracted twice with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8fa5155bef7641809da1867f7da36c9d
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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