Ortho-substituent effect promoted rapid cleavage of amide C-N bond under mild conditions

This article reports the ortho-substituent effect on the cleavage of the amide C-N bond. In the structure of N a -Phth-N-pyridinyl-amide, when the hydrogen atom in the 3-position of pyridine ring was replaced by alkoxy group, the amide C-N cleavage can take place in the 2-position of the pyridine ring. This transfor- mation can proceed rapidly in methylamine ethanol solution under mild conditions to afford 2-amino-3-alkoxy pyridines.