Ammonia → HCID 23462097, compound

Participants

Reaction Steps

In a 300 cc, three-neck flask, equipped with a stirrer and dropping funnel, was made 0.2 mole of sodamide in liquid ammonia. The ammonia was replaced with 100 cc of xylene. A thermometer and reflux condenser were attached to the reaction flask, and the mixture was heated to reflux. Under reflux, 24.1 g (0.16 mole) of 2-isoamylpyridine was added from the dropping funnel. The reaction mixture turned to a deep purple and hydrogen began evolving. Refluxing was continued for 6.5 hours. The temperature range was 140°-146° C. At the end of the reflux, the reaction mixture was cooled to about 100° C. and hydrolyzed with 50 cc of water. The oil layer was separated at room temperature and the aqueous layer was extracted with 22 cc of xylene. The oil layer and xylene extract were distilled through a Vigreaux column to give 15.3 g of 2-isoamylpyridine (0.10 mole), 0.8 g of 2-amino-6-isoamylpyridine (8.2% yield) and 3.4 g of 6,6'-di-isoamyl-2,2'-bipyridyl (38.9% yield).

Provenance & Evidence