Nitration of 3-Methylaceperidazines with a Large Excess of Fuming Nitric Acid

Abstract

Nitration of N-acetyl-3-methylaceperidazine with a 2–3-fold excess of nitric acid (d 1.36, 1.48) in glacial acetic acid results in the exclusive formation of mono- and dinitroderivatives. The nitration of 3-methylaceperidazine and its N-alkyl- and N-acetyl-substituted derivatives with a 6–9-fold excess of fuming nitric acid (d 1.54) in the same conditions results in the formation of both the expected products of mono- and dinitration and a product of the electrophilic addition of nitric acid to a double bond of acenaphthene scaffold of the molecule of nitration product.