Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes - 25/03/13

, Ana B. Miltojević a
, Rastko D. Vukićević b 
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Graphical abstract |
Abstract |
A one-pot solvent-free synthesis of N-methyl imines in good to excellent yields was performed by grinding together aromatic aldehydes and methylamine hydrochloride in the presence of a base. The best yields were achieved when an excess of methylamine hydrochloride and inexpensive sodium hydrogen carbonate was used (usually in a molar ratio ArCHO/CH3NH2·HCl/NaHCO3=1:5:5), allowing the reaction to proceed for 1h (in the case of aromatic aldehydes containing electron-withdrawing substituents) or overnight (in the case of electron-rich aldehydes). After a simple work-up (extraction with diethyl ether) the obtained products were mostly pure enough for spectral characterization. In this way, 31 N-methyl imines were prepared, among which eight were synthesized for the first time. Their structures were elucidated by spectral means (1H- and 13C-NMR, IR, MS) whenever it was possible. In the case of salicylaldehyde and 4-chlorobenzaldehyde, the synthesis of the corresponding imines was also conducted on a gram-scale with a 72% and 84% isolated yield, respectively. The present approach not only provides good to high yields, but also eliminates the disadvantages of the traditional synthesis of N-methyl imines, such as the use of hazardous solvents and more or less expensive catalysts and the necessity of work/handling with an anhydrous gas in pressurized containers.
Le texte complet de cet article est disponible en PDF.Keywords : Aromatic aldehydes, Methylamine hydrochloride, N-methyl imines, One-pot synthesis, Solvent-free
Plan
Vol 16 - N° 3
P. 257-270 - mars 2013 Retour au numéroBienvenue sur EM-consulte, la référence des professionnels de santé.
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