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Preparation of carbon 14‐labelled “Spy Dust” 5‐(4‐nitrophenyl)‐2,4‐[5‐ 14 C]pentadienal, (NPPD)
Author(s) -
Brown Susan I.,
Rotert Gary A.,
Lamontagne Maurice P.
Publication year - 1987
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.2580241108
Subject(s) - chemistry , nitrobenzene , yield (engineering) , ylide , benzaldehyde , hydride , nitro , carbon 14 , carbon fibers , nitro compound , medicinal chemistry , organic chemistry , nuclear chemistry , catalysis , hydrogen , materials science , alkyl , physics , quantum mechanics , composite number , metallurgy , composite material
Abstract Preparation of carbon 14‐labelled “Spy Dust”, 5‐(4‐nitrophenyl)‐2,4‐[5‐ 14 C]pentadienal is described. The facile synthesis of 4‐nitro[formyl‐ 14 C]benzaldehyde from 1‐iodo‐4‐nitrobenzene by reaction with K 14 CN/CuCN, followed by reduction with diisobutylaluminum hydride provided this key intermediate in 50% yield. Subsequent treatment with the resonance‐stabilized ylide, formylmethylenetriphenylphosphorane, afforded the title compound.