The general procedure for the synthesis of 6-(chloromethyl)quinoxaline from 6-methylquinoxaline is as follows:
Example 1: Catalytic air dehydrogenation of 6-hydroxymethyl-methyl-quinoxaline
In a 500 mL round-bottomed flask, 6-methylquinoxaline (10 g, 69.4 mmol) was dissolved in 240 g of acetonitrile with N-chlorosuccinimide (14 g, 105.3 mmol). Benzoyl peroxide (0.4 g, 1.65 mmol) was added as initiator. A reflux condenser was installed and the reaction mixture was heated and refluxed for 6 hours, followed by the addition of benzoyl peroxide (0.1 g). The reflux reaction was continued for a total reaction time of 12 hours. Upon completion of the reaction, the reaction solution was analyzed by gas chromatography (GC), which showed the generation of 6-(chloromethyl)quinoxaline with 80% selectivity and 60% conversion.
