Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/10346
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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