Acetic Anhydride → 1H-Indole-2,3-dione, 1-acetyl-5-methyl-

HRID 6359

Reaktionsgleichung

Reaktionsgleichung von HRID 6359
[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:12].[H-].[Na+].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2)[C:5](=[O:12])[C:6]1=[O:11])(=[O:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 118405-MethylisatinHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 5399471H-Indole-2,3-dione, 1-acetyl-5-methyl-Ausbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

With stirring at 0° C., 8.06 g (50.0 mmols) of 5-methylisatin was added by small portions to a solution of 2.00 g (50.0 mmols) of sodium hydride in toluene. While stirring under ice cooling, 4.7 ml (50.0 mmols) of acetic anhydride was dropwise added to the mixture followed by heating at 80° C. for further an hour with stirring. After completion of the reaction, an aqueous saturated sodium bicarbonate solution was added to the reaction mixture. The crystals were filtered, washed with water and dried to give 4.84 g (yield, 47%) of 1-acetyl-5-methylisatin.

Aufarbeitung

  1. stirringWhile stirring under ice cooling
  2. temperatureby heating at 80° C. for further an hour
  3. stirringwith stirring
  4. customAfter completion of the reaction
  5. filtrationThe crystals were filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b0cbbbccef144c919960c98519e95613
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248684

Verknüpfte Notizen

Wird geladen…