Synthesis of 13C and 15N labeled 2,4-dinitroanisole.

Syntheses of [C-13(6)]-2,4-dinitroanisole (ring-C-13(6)) from [C-13(6)]-anisole (ring-C-13(6)) and [N-15(2)]-2,4-dinitroanisole from anisole using in situ generated acetyl nitrate and [N-15]-acetyl nitrate, respectively, are described. Treatment of [C-13(6)]-anisole (ring-C-13(6)) with acetyl nitrate generated in 100% HNO3 gave [C-13(6)]-2,4-dinitroanisole (ring-C-13(6)) in 83% yield. Treatment of anisole with [N-15]-acetyl nitrate generated in 10N [N-15]-HNO3 gave [N-15(2)]-2,4-dinitroanisole in 44% yield after two cycles of nitration. Byproducts in the latter reaction included [N-15]-2-nitroanisole and [N-15]-4-nitroanisole.