Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone

The influence of temperature, reaction time, and type of the catalyst on the yield of the 2,3,5-trimethylpyridine (collidine) from 3-amino-2-methylpropenal and methylethylketone was investigated. 3-Amino-2-methylpropenal was synthesized from 3-ethoxy-2-methylacrolein previously synthesized from meth...

Full description

Bibliographic Details
Main Authors: Urošević Jovica, Mitić Miroslav, Arsić Biljana, Stojanović Gordana
Format: Article
Language:English
Published: Serbian Chemical Society 2022-01-01
Series:Journal of the Serbian Chemical Society
Subjects:
Online Access:http://www.doiserbia.nb.rs/img/doi/0352-5139/2022/0352-51392200042U.pdf
_version_ 1828171823030730752
author Urošević Jovica
Mitić Miroslav
Arsić Biljana
Stojanović Gordana
author_facet Urošević Jovica
Mitić Miroslav
Arsić Biljana
Stojanović Gordana
author_sort Urošević Jovica
collection DOAJ
description The influence of temperature, reaction time, and type of the catalyst on the yield of the 2,3,5-trimethylpyridine (collidine) from 3-amino-2-methylpropenal and methylethylketone was investigated. 3-Amino-2-methylpropenal was synthesized from 3-ethoxy-2-methylacrolein previously synthesized from methylmalondialdehyde tetraethyl acetal, obtained from triethyl orthoformate and propenyl ether. The optimal conditions for the investigated synthesis were temperature of 150 °C, reaction time 24 h, and the CH3COOH/pTsOH catalyst. This synthesis is the first successful attempt to synthesize 2,3,5-trimethylpyridine in an acid medium.
first_indexed 2024-04-12T03:31:24Z
format Article
id doaj.art-b2bef4e08f374877b135fdc5f432e39d
institution Directory Open Access Journal
issn 0352-5139
1820-7421
language English
last_indexed 2024-04-12T03:31:24Z
publishDate 2022-01-01
publisher Serbian Chemical Society
record_format Article
series Journal of the Serbian Chemical Society
spelling doaj.art-b2bef4e08f374877b135fdc5f432e39d2022-12-22T03:49:32ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212022-01-0187101117112310.2298/JSC210918042U0352-51392200042UOptimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketoneUrošević Jovica0Mitić Miroslav1https://orcid.org/0000-0003-3658-9921Arsić Biljana2https://orcid.org/0000-0002-1248-5864Stojanović Gordana3https://orcid.org/0000-0002-3128-6510Chemical-technological school “Božidar Đorđevic Kukar”, Leskovac, SerbiaChemical-technological school “Božidar Đorđevic Kukar”, Leskovac, SerbiaUniversity of Niš, Faculty of Sciences and Mathematics, Department of Chemistry, Niš, SerbiaUniversity of Niš, Faculty of Sciences and Mathematics, Department of Chemistry, Niš, SerbiaThe influence of temperature, reaction time, and type of the catalyst on the yield of the 2,3,5-trimethylpyridine (collidine) from 3-amino-2-methylpropenal and methylethylketone was investigated. 3-Amino-2-methylpropenal was synthesized from 3-ethoxy-2-methylacrolein previously synthesized from methylmalondialdehyde tetraethyl acetal, obtained from triethyl orthoformate and propenyl ether. The optimal conditions for the investigated synthesis were temperature of 150 °C, reaction time 24 h, and the CH3COOH/pTsOH catalyst. This synthesis is the first successful attempt to synthesize 2,3,5-trimethylpyridine in an acid medium.http://www.doiserbia.nb.rs/img/doi/0352-5139/2022/0352-51392200042U.pdfcyclic condensationgc-msside reactions
spellingShingle Urošević Jovica
Mitić Miroslav
Arsić Biljana
Stojanović Gordana
Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
Journal of the Serbian Chemical Society
cyclic condensation
gc-ms
side reactions
title Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
title_full Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
title_fullStr Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
title_full_unstemmed Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
title_short Optimization of the reaction conditions for the synthesis of 2,3,5-trimethylpyridine from 3-amino-2-methylpropenal and methylethylketone
title_sort optimization of the reaction conditions for the synthesis of 2 3 5 trimethylpyridine from 3 amino 2 methylpropenal and methylethylketone
topic cyclic condensation
gc-ms
side reactions
url http://www.doiserbia.nb.rs/img/doi/0352-5139/2022/0352-51392200042U.pdf
work_keys_str_mv AT urosevicjovica optimizationofthereactionconditionsforthesynthesisof235trimethylpyridinefrom3amino2methylpropenalandmethylethylketone
AT miticmiroslav optimizationofthereactionconditionsforthesynthesisof235trimethylpyridinefrom3amino2methylpropenalandmethylethylketone
AT arsicbiljana optimizationofthereactionconditionsforthesynthesisof235trimethylpyridinefrom3amino2methylpropenalandmethylethylketone
AT stojanovicgordana optimizationofthereactionconditionsforthesynthesisof235trimethylpyridinefrom3amino2methylpropenalandmethylethylketone