Methanolysis of Benzoyl hydrazines in the presence of Trifluoromethanesulfonic acid

Abstract

Methanolysis of variously substituted benzoyl hydrazines in the presence of CF3SO3H was explored for the first time. The effects of CF3SO3H acid concentration and substituents attached to benzoyl hydrazine on yield and reaction times were also examined. It was found that doubling the acid concentration results in an approximately four-fold decrease in reaction times. Moreover, reaction times are strongly dependent on the nature of substituents. Presence of electron-donating substitutes increases the reaction rate, while presence of electron-withdrawing groups has the opposite effect. The obtained results clearly demonstrate that acyl hydrazines could be converted to esters in good to excellent yields in the presence of 6-9 eq of CF3SO3H.