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

HRID 366592

Reaktionsgleichung

Reaktionsgleichung von HRID 366592
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Bromo-2-nitrophenylacetic acid (0.26 g), 0.26 g zinc powder and 3 mL 50% sulfuric acid in 5 mL of ethanol were 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6eb115e3539c4995a32bf95b4013b39e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130238

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