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Synthesis of 13 C and 15 N labeled 2,4‐dinitroanisole
Author(s) -
Jagadish Bhumasamudram,
Field Jim A.,
Chorover Jon,
SierraAlvarez Reyes,
Abrell Leif,
Mash Eugene A.
Publication year - 2014
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3192
Subject(s) - anisole , chemistry , nitration , yield (engineering) , ring (chemistry) , nitrate , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Syntheses of [ 13 C 6 ]‐2,4‐dinitroanisole (ring‐ 13 C 6 ) from [ 13 C 6 ]‐anisole (ring‐ 13 C 6 ) and [ 15 N 2 ]‐2,4‐dinitroanisole from anisole using in situ generated acetyl nitrate and [ 15 N]‐acetyl nitrate, respectively, are described. Treatment of [ 13 C 6 ]‐anisole (ring‐ 13 C 6 ) with acetyl nitrate generated in 100% HNO 3 gave [ 13 C 6 ]‐2,4‐dinitroanisole (ring‐ 13 C 6 ) in 83% yield. Treatment of anisole with [ 15 N]‐acetyl nitrate generated in 10 N [ 15 N]‐HNO 3 gave [ 15 N 2 ]‐2,4‐dinitroanisole in 44% yield after two cycles of nitration. Byproducts in the latter reaction included [ 15 N]‐2‐nitroanisole and [ 15 N]‐4‐nitroanisole.