Réaction #51695

Équation de réaction

water

(6-chloro-indol-1-yl)-acetonitrile

dichloromethylene dimethylammonium chloride

→

6-chloro-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide

Rendement 46.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températureto reflux for 14 h
2. 2
   ExtractionThe mixture was extracted into ethyl acetate
3. 3
   Autrepurified by column chromatography (silica gel, hexane:ethyl acetate 3:7)

Mode opératoire

To a solution of (6-chloro-indol-1-yl)-acetonitrile (0.446 g, 2.34 mmole) in acetonitrile (30 ml) was added dichloromethylene dimethylammonium chloride (phosgene imminium chloride) (0.418 g, 2.57 mmole). The reaction mixture was brought to reflux for 14 h and then poured into water (100 ml). The mixture was extracted into ethyl acetate and purified by column chromatography (silica gel, hexane:ethyl acetate 3:7) to afford the desired 6-chloro-1-cyanomethyl-1H-indole-3-carboxylic acid dimethylamide (0.286 g, 46% yield) in addition to recovered starting material (0.173 g). Step 3

Source