Koji Sakai, T. Ito, Ken-ichi Watanabe
Jul 1, 1967
Citations
0
Influential Citations
19
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
When 2-cyanopyridine is refluxed with water in the presence of nickel or copper oxide, it is easily hydrolyzed and affords a chelate compound of the acid with nickel or copper. On the other hand, 3- or 4-cyanopyridine affords only the corresponding free amide by the same reaction. The interfering effect of thiophene is not observed in the reaction of 2-cyanopyridine, but it is observed in the case of the 3- or 4-cyanopyridine. When 2-cyanopyridine is refluxed with an aqueous solution of nickel or cupric chloride, it is hydrated to form a chelate of the amide with nickel or copper. These chelates are hydrolyzed with the metal oxides in water to afford the chelates of the acid. Pyridine-2-carboxylic acid amide is also hydrolyzed to the chelate of the acid, but the hydrolysis of the 3- or 4-amide isomer does not occur under the same conditions. The four chelates of the acid and amide are excellent catalysts for the hydration of 2-cyanopyridine, giving the free amide in a high yield. From these facts, it may ...