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Comptes Rendus Chimie
,  volume 16 ,  issue 3 ,  pages 257-270

Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes

Publication type: Journal Article
Publication date: 2013-03-01
Cellule MathDoc/Centre Mersenne
scimago Q3
wos Q4
SJR: 0.209
CiteScore: 2.3
Impact factor: 0.6
ISSN: 16310748, 18781543
General Chemistry
General Chemical Engineering
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.
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GOST Copy
Radulović N. et al. Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes // Comptes Rendus Chimie. 2013. Vol. 16. No. 3. pp. 257-270.
GOST all authors (up to 50) Copy
Radulović N., Radulović N. S., Miltojevic A., Miltojević A. B., Vukićević R. D. Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes // Comptes Rendus Chimie. 2013. Vol. 16. No. 3. pp. 257-270.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.crci.2013.01.010
UR - https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2013.01.010/
TI - Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes
T2 - Comptes Rendus Chimie
AU - Radulović, Niko
AU - Radulović, Niko S
AU - Miltojevic, Ana
AU - Miltojević, Ana B
AU - Vukićević, Rastko D.
PY - 2013
DA - 2013/03/01
PB - Cellule MathDoc/Centre Mersenne
SP - 257-270
IS - 3
VL - 16
SN - 1631-0748
SN - 1878-1543
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Radulović,
author = {Niko Radulović and Niko S Radulović and Ana Miltojevic and Ana B Miltojević and Rastko D. Vukićević},
title = {Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes},
journal = {Comptes Rendus Chimie},
year = {2013},
volume = {16},
publisher = {Cellule MathDoc/Centre Mersenne},
month = {mar},
url = {https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2013.01.010/},
number = {3},
pages = {257--270},
doi = {10.1016/j.crci.2013.01.010}
}
MLA
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MLA Copy
Radulović, Niko, et al. “Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes.” Comptes Rendus Chimie, vol. 16, no. 3, Mar. 2013, pp. 257-270. https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2013.01.010/.