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Preparation of deuterated toluidines and xylidines
Author(s) -
Frischkorn C. G. B.,
Kohler H.,
Rose B.,
Unterlugauer D.,
Conrad H. M.
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.2580140405
Subject(s) - chemistry , deuterium , yield (engineering) , ring (chemistry) , side chain , tritium , medicinal chemistry , organic chemistry , materials science , physics , quantum mechanics , metallurgy , polymer , nuclear physics
Deuteration in definite positions of the aromatic ring system or in the side chain of different methyl anilines is achieved in D 2 O under different conditions: at 150°C and pH 3 deuteration occurs in ortho/para positions; whereas at 250°C and pH 3 a total deuteration of the aromatic system takes place (overall deuteration 82–99%). Perdeuteration (81–99% in the aromatic ring, 60–99% in the side chain) is obtained in high acidic medium (pH ⩽ 1) and at 250°C. The yield of the deuterated methyl anilines is generally high (40–100%) so that this reaction is a more attractive route for preparing methyl anilines and their derivatives than the conventional ways of synthesis. By using T 2 O instead of D 2 O it should be possible to prepare the appropriate tritium‐labelled compounds.