Reaktion #3205

ord-ed246c15161e44ccb5ed8c113f70f2e4

Reaktionsgleichung

Cc1cc(C)c2c(c1)NC(=O)C2=O
4,6-dimethyl-1H-indole-2,3-dione
O
water
→
Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1
title compound
Ausbeute 31.0%
Cc1cc(C)c2c(=O)oc(=O)[nH]c2c1
5,7-Dimethyl-2H-3,1-benzoxazine-2,4(1H)-dione
Ausbeute 31.0%

Edukte

Cc1cc(C)c2c(c1)NC(=O)C2=O
4,6-dimethyl-1H-indole-2,3-dione
O
water

Reagenzien

[Cr+6].[O-2].[O-2].[O-2]
chromium trioxide

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwhile maintaining the temperature of the reaction mixture at 65°-70° C
  2. 2
    Temperaturcooled
  3. 3
    Filtrationfiltered

Vorschrift

To a stirred warm (60° C.) solution of 4,6-dimethyl-1H-indole-2,3-dione (2.0 g, 11.4 mM) in acetic acid (20 mL) was added in small portions chromium trioxide (6.6 g, 66 mM) while maintaining the temperature of the reaction mixture at 65°-70° C. The reaction mixture was then heated at 80° C. for one hour, cooled, poured into water (150 mL) and filtered to obtain the the title compound (0.67 g, 31%) as a light yellow solid; MS(CI): 192 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733910uspto-grants-1998_03