2,5-Dichlorobenzoic acid → HCID 23337819, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 19.1 g. of 2,5-dichlorobenzoic acid [Besley & Goldberg, J. Chem. Soc., 2448 (1954)] in 100 ml. of amyl alcohol is added 6.9 g. of anhydrous potassium carbonate and 0.1 g. of copper oxide. The mixture is stirred and heated at 100° C. for 30 minutes, then 13.0 g. of 5-amino-2-methoxypyridine is added and the mixture is heated at reflux and stirred for 3 hours. A small amount of water forms and is collected in a Dean-Stark apparatus. The reaction mixture is cooled, poured into water and made basic with potassium carbonate. The mixture is steam-distilled to remove the amyl alcohol, then filtered and the filtrate is acidified to pH 6. The mixture is again filtered and this pink filtrate is acidified with 6 N hydrochloric acid to pH 4. The solid is collected, giving 5-chloro-2-(6-methoxy-3-pyridylamino)benzoic acid as a pink crystalline solid.

Provenance & Evidence