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Synthesis of 5‐nitrofuran‐2 [ 14 C] aldehyde diacetate and the antibacterial agent [ 14 C]‐nifuroxazide
Author(s) -
Elsom L. F.,
Hawkins D. R.
Publication year - 1978
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.2580140602
Subject(s) - chemistry , aldehyde , yield (engineering) , nitrofuran , furan , hydrolysis , organic chemistry , catalysis , medicinal chemistry , materials science , biology , metallurgy , genetics
Furan‐2‐[ 14 C] carboxylic acid has been prepared in 74% yield by carbonation of 2‐furyl‐lithium. Furan‐2‐[ 14 C] aldehyde was isolated as the diacetate after catalytic reduction of the corresponding acid chloride. Nitration gave 5‐nitrofuran‐2‐[ 14 C] aldehyde diacetate and after hydrolysis to the aldehyde was condensed with 4‐hydroxybenzhydrazide to give 5‐nitrofuran‐2‐[ 14 C]‐aldehyde 4′‐hydroxybenzoylhydrazone, [ 14 C]‐nifuroxazide, in an overall radiochemical yield of 15% from barium [ 14 C]‐carbonate.