Reaktion #50672

Reaktionsgleichung

2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione

oxalyl chloride

pyrrole-2-carboxylic acid

tin (IV) chloride

→

product

Ausbeute 69.2%

2-[2-(1H-Pyrrol-2-ylcarbonyl)-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)dione

Ausbeute 69.2%

Lösungsmittel

water

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturunder reflux for 1 hour
3. 3
   workup.STIRRINGby stirring at -10° C. for additional 30 minutes
4. 4
   Extraktionextracted with DCM
5. 5
   WaschenThe combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid
6. 6
   TrocknenThe dried (magnesium sulfate) organic phase
7. 7
   Filtrationwas filtered
8. 8
   Sonstigeevaporated in vacuo
9. 9
   SonstigeThe residue was triturated with DCM

Vorschrift

To a suspension of pyrrole-2-carboxylic acid (5.55 g) in 500 ml of DCM was added oxalyl chloride (8.7). The reaction mixture was heated under reflux for 1 hour, cooled to -10° C., and tin (IV) chloride (5.85 ml) was added. After stirring the mixture at -10° C. for 30 minutes, 2-(1H-pyrrol-1-yl)-1H-isoindole-1,3(2H)dione (10.6 g) was added in four portions over a period of 30 minutes, followed by stirring at -10° C. for additional 30 minutes. The reaction mixture was then poured into 500 ml of water and extracted with DCM. The combined extracts were washed with 1N sodium hydroxide solution, 1N sulfuric acid, and finally with water. The dried (magnesium sulfate) organic phase was filtered and evaporated in vacuo. The residue was triturated with DCM, affording the product as a powder (10.55 g), mp 204°-206° C.

Quelle