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Preparation of nicotinic‐5‐ 2 H acid from 5‐bromonicotinic acid
Author(s) -
Clark Brian R.
Publication year - 1976
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.2580120408
Subject(s) - chemistry , deuterium , nicotinic agonist , tetrahydrofuran , nuclear magnetic resonance spectroscopy , hydrolysis , spectroscopy , yield (engineering) , molecule , nuclear chemistry , mass spectrometry , medicinal chemistry , organic chemistry , chromatography , biochemistry , physics , receptor , materials science , quantum mechanics , solvent , metallurgy
Methyl nicotinate‐5‐ 2 H was prepared in dry tetrahydrofuran by palladium‐catalyzed deuterolysis of methyl 5‐bromonicotinate. Acid hydrolysis of the crude reaction mixture resulted in a 92% yield of deuterium‐labeled nicotinic acid of which 80 mole% was nicotinic‐5‐ 2 H acid and 12 mole% was nicotinic‐5‐ 2 H acid containing an additional deuterium atom elsewhere in the molecule. The structure assignment was based on the results of nuclear magnetic resonance spectroscopy, mass spectroscopy, ultraviolet spectroscopy, and elemental analysis.