Triethylamine → HCID 19780237, compound

Participants

Reaction Steps

Trimethylsilyl cyanide (36.15 g, 48.6 ml, 0.36 moles) was added dropwise to a solution of 2-(o-chlorobenzyl)-pyridine-N-oxide (32.0 g, 0.15 moles) and triethylamine (22.13 g, 30.5 ml, 0.22 moles) in acetonitrile (100 ml) at 20° C. under a nitrogen atmosphere. After complete addition the reaction mixture was heated under reflux for 48 hours, cooled to room temperature and partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic layer was washed with water and saturated sodium chloride solution and was then dried over anhydrous magnesium sulphate. Removal of the solvent gave an orange brown oil which was purified by column chromatography (silica gel eluted with hexane:ethyl acetate 4:1) to give 2-(o-chlorobenzyl)-6-cyanopyridine (11.5 g, 35%) as a pale yellow oil.

Provenance & Evidence