Reaktion #466905

Reaktionsgleichung

acetyl chloride

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

pyridine

→

titled compound

Ausbeute 54.0%

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

Ausbeute 54.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml)
2. 2
   ExtraktionThe organic extract
3. 3
   Waschenwas washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml)
4. 4
   SonstigeAfter drying
5. 5
   Sonstige(MgSO4) and removal of solvent
6. 6
   Sonstigethe crude product was purified by flash chromatography
7. 7
   Wascheneluting with ethyl acetate/hexane (1:1)

Vorschrift

To a solution of 3-amino-2-benzoyl-6-chloro-1-(ethoxycarbonyl)indole (300 mg, 0.88 mmol; example 1, step 2) in a mixture of dichloromethane (10 ml) and pyridine (0.08 ml, 0.96 mmol) was added acetyl chloride (0.07 ml, 0.96 mmol). After stirring for 4 h, the mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml). The organic extract was washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). After drying (MgSO4) and removal of solvent, the crude product was purified by flash chromatography eluting with ethyl acetate/hexane (1:1) to afford 183 mg (54%) of the titled compound as a yellow oil.

Quelle