In a two-liter, three-neck flask, equipped with a stirrer and dropping funnel, was prepared 0.20 mole of sodamide, using an iron catalyst, in about 600 cc of liquid ammonia. The ammonia was replaced by adding 1,000 g of N,N-dimethylaniline through the dropping funnel and evaporating the ammonia. A thermometer and reflux condenser were added to the flask. The mixture was heated to 152° C. and 205 g (1.0 mole) of 2-(5-nonyl)pyridine was added. No reaction took place. The mixture was slowly heated to 197° C. when hydrogen evolution started, and the reaction mixture turned purple. The reaction continued at 197°-198° C. for 3 hours, at which time the hydrogen evolution became slow. The reaction mixture was cooled to about room temperature and hydrolyzed with 200 cc of water. The oil layer was separated and distilled to give 125 g (0.61 mole) of unreacted 2-(5-nonyl)pyridine, 2.3 g (0.01 mole) of 2-amino-(5-nonyl)pyridine (2.7% yield) and 35.8 g (0.09 mole) of 6,6'-di-(5-nonyl)-2,2'-bipyridyl boiling at 251°-259° C. and 7 mm Hg. The yield of 2,2'-bipyridyl product based on recovered 2-(5-nonyl)pyridine was 45.0%.
