Reaktion #161238

Reaktionsgleichung

N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl)acetamide

sodium formate

sodium acetate

→

1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone

Ausbeute 88.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationthe mixture was filtered through Celite
3. 3
   WaschenThe Celite was washed with EtOAc
4. 4
   Waschenthe combined filtrates were washed with sat. NaHCO3
5. 5
   WaschenThe separated organic layer was washed with water and brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure

Vorschrift

A solution of N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl)acetamide (3.1 g, 10.2 mmol), tetraethylammonium chloride hydrate (2.4 g, 149 mmol), sodium formate (1.08 g, 18 mmol), sodium acetate (2.76 g, 34.2 mmol) and palladium acetate (0.32 g, 13.2 mmol) in anhydrous DMF (50 mL) was stirred at 80° C. for 15 h under N2 atmosphere. After cooling, the mixture was filtered through Celite. The Celite was washed with EtOAc and the combined filtrates were washed with sat. NaHCO3. The separated organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure to provide 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone as a brown solid (2.1 g, 88%).

Quelle