Hydrochloric Acid → 5-Methylindolin-2-one

HRID 24545

Reaktionsgleichung

Reaktionsgleichung von HRID 24545
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.O.NN.Cl>C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 118405-MethylisatinHCID 24654Hydrazine hydrate (1:1)

Produkt 1

HCID 53257165-Methylindolin-2-oneAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

5-Methylisatin (15.0 g) and 60 mL of hydrazine hydrate were heated to 140-160° C. for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed no starting material remaining. The reaction mixture was cooled to room temperature, poured into 300 mL of ice water, and acidified to pH 2 with 6 N hydrochloric acid. After standing at room temperature for 2 days, the precipitate was collected by vacuum filtration, washed with water, and dried under vacuum to give 6.5 g (47%) of 5-methyl-2-oxindole.

Aufarbeitung

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washwashed with water
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-87c94434fa3d4c069c16f4dc7bf9e816
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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