Synthesis of the  15 N‐labelled insecticide imidacloprid | Zendy

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Synthesis of the 15 N‐labelled insecticide imidacloprid

Author(s) -

Schippers Nicole,

Schwack Wolfgang

Publication year - 2006

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.1042

Subject(s) - chemistry , imidacloprid , neonicotinoid , pyridine , yield (engineering) , imine , nicotinic agonist , medicinal chemistry , organic chemistry , radiochemistry , pesticide , catalysis , biochemistry , materials science , receptor , agronomy , metallurgy , biology

A five‐step synthesis of the neonicotinoid insecticide imidacloprid ( 1 ) labelled with 15 N is reported in an overall yield of 10%. The stable isotope 15 N was introduced in the pyridine part by reaction of 15 NH 3 with coumalic acid methyl ester ( 2 ) to 15 N ‐hydroxy nicotinic acid ( 3 ) followed by further reactions to 15 N ‐2‐chloro‐5‐(chloromethyl) pyridine ( 6 ) which was coupled with N ‐nitroimidazolidin‐2‐imine to yield 1 . Copyright © 2006 John Wiley & Sons, Ltd.

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