Reaktion #466906

Reaktionsgleichung

3-acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole

KOH

→

title compound

Ausbeute 41.1%

3-Acetylamino-2-benzoyl-6-chloroindole

Ausbeute 41.1%

Lösungsmittel

ethanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux temperature for 1 h
3. 3
   TemperaturThe mixture was cooled
4. 4
   Einengenconcentrated
5. 5
   Sonstigethe residue partitioned between water (50 ml) and diethyl ether (100 ml)
6. 6
   ExtraktionThe organic extract
7. 7
   Waschenwas washed with water (100 ml)
8. 8
   SonstigeAfter drying
9. 9
   Sonstige(MgSO4) and removal of solvent
10. 10
    Sonstigethe crude product was recrystallized from dichloromethane/hexane

Vorschrift

To a solution of 3-acetylamino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (556 mg, 1.4 mmol) in ethanol/water (3:1, 20 ml) was added KOH (85% pellets, 480 mg, 7.2 mmol) and the mixture was heated at reflux temperature for 1 h. The mixture was cooled and concentrated, and the residue partitioned between water (50 ml) and diethyl ether (100 ml). The organic extract was washed with water (100 ml) and then brine (100 ml). After drying (MgSO4) and removal of solvent, the crude product was recrystallized from dichloromethane/hexane to afford 180 mg (41%) of the title compound as a yellow powder. m.p.: 212-213° C. 1H-NMR (CDCl3) δ: 9.90 (1H, br s), 8.29-8.15 (2H, m), 7.84-7.75 (2H, m), 7.70-7.52 (3H, m), 7.32-7.27 (1H, m), 7.12 (1H, dd, J=1.83, 9.16 Hz), 2.26 (3H, s). IR (KBr) ν: 3400, 1680, 1640, 1520, 1320 cm−1

Quelle