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Title: | Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes |
Authors: | Radulovic, Niko Miltojevic, Ana Vukicevic, Rastko |
Issue Date: | 2013 |
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 1 h (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. © 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved. |
URI: | https://scidar.kg.ac.rs/handle/123456789/10346 |
Type: | article |
DOI: | 10.1016/j.crci.2013.01.010 |
ISSN: | 1631-0748 |
SCOPUS: | 2-s2.0-84875367570 |
Appears in Collections: | Faculty of Science, Kragujevac |
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