Isoquinoline → 2-(3-Methylbutyl)isoquinolin-2-ium iodide

Participants

Reaction Steps

To 15.3 g of isoamyliodide and 10 g of isoquinoline placed in a four-necked flask equipped with a reflux condenser and mechanical stirrer was added 30 ml of ethanol. The mixture was reacted for 3 hours under reflux. When the reaction was completed, ethanol was removed from the reaction mixture under reduced pressure, the residue was washed 2-times with 45 ml of ethyl ether. 23.0 g of N-isoamylisoquinolinium iodide was obtained as yellow crystals. Subsequently, into a four-necked flask equipped with a reflux condenser and mechanical stirrer was placed 8 g of TCNQ and 280 ml of acetonitrile, and the TCNQ was dissolved in the acetonitrile under reflux. To the flask was added a solution of 9.6 g of N-isoamylisoquinolinium iodide in 40 ml of acetonitrile, and the mixture was reacted for 20 minutes under reflux. The reaction mixture was cooled to 5° C., separated black needles were filtered out and washed 2-times with 100 ml of methanol. 10.4 g of charge transfer complex of N-isoamylisoquinolinium TCNQ was obtained. The infra-red spectrum of the complex was shown in FIG. 3. The specific resistance of the complex measured by the same method as that described in Example 1 was 3.6 Ωcm.

Provenance & Evidence