SYNTHESIS OF 2-(2'-HYDROXYPHENYL)PYRIDINE-N-OXIDE AND ITS THERMAL DECOMPOSITION AS A MODEL REACTION OF ORELLANINE DEOXIDATION

Article abstract of DOI:10.1016/0040-4039(84)80062-3

2-Methoxyphenylmagnesium bromide was reacted with 2-nitropyridine-N-oxide and demethylated to give 2-(2'-hydroxyphenyl)pyridine-N-oxide (II) which was found to undergo a thermal deoxidation to the free base (VI); the process is interpreted as a <1.5> oxygen shift followed by decomposition of the hydroperoxide intermediate.