Preparation of carbon 14‐labelled “Spy Dust” 5‐(4‐nitrophenyl)‐2,4‐[5‐ 14 C]pentadienal, (NPPD) | Zendy

Brown Susan I. | Zendy; Rotert Gary A. | Zendy; Lamontagne Maurice P. | Zendy

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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

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.

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