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

HRID 1815405Notes

Reaction equation

HRID 1815405 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 and 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
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-25e997ce60514940b5876b80493365c9
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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