RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE

ABSTRACT Diethyl 2-((4-nitroanilino)methylene)malonate [4-NANM-E] is an important molecule owing to its role of precursor in the multistage synthesis of several quinoline derivatives possessing biological activities such as antiviral, immunosuppressive, anticancer and photoprotector. This molecule i...

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Autores principales:	Valle,Hernán, Mangalaraja,Ramalinga Viswanathan, Rivas,Bernabé L., Becerra,José, Naveenraj,Selvaraj
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2018
Materias:	Anilinomethylenemalonate Room temperature synthesis Quinoline Methanolysis
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304098
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spelling	oai:scielo:S0717-970720180003040982018-10-03RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATEValle,HernánMangalaraja,Ramalinga ViswanathanRivas,Bernabé L.Becerra,JoséNaveenraj,Selvaraj Anilinomethylenemalonate Room temperature synthesis Quinoline Methanolysis ABSTRACT Diethyl 2-((4-nitroanilino)methylene)malonate [4-NANM-E] is an important molecule owing to its role of precursor in the multistage synthesis of several quinoline derivatives possessing biological activities such as antiviral, immunosuppressive, anticancer and photoprotector. This molecule is usually synthesized by a nucleophilic vinyl substitution (SNV) between 4-nitroaniline and diethylethoxymethylene malonate (EMA). Although several procedures are available to synthesize 4-NANM-E in liquid phase, more convenient method is necessary to synthesize in less reaction time and at room temperature. In this study, it is demonstrated that equimolar amounts of EMA and 4-nitroaniline dissolved in alcoholic KOH react within a few seconds at room temperature to produce 4-NANM-E which is purified by simple filtration after acidification with aqueous HCl and washing with alcohol. The reaction has the yield varying at the range 45-53% when it occurs in ethanol, 2-propanol, 2-butanol or 2-pentanol. Therefore, this synthesis method is an excellent alternative to produce 4-NANM-E on an industrial scale.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.63 n.3 20182018-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304098en10.4067/s0717-97072018000304098
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Anilinomethylenemalonate Room temperature synthesis Quinoline Methanolysis
spellingShingle	Anilinomethylenemalonate Room temperature synthesis Quinoline Methanolysis Valle,Hernán Mangalaraja,Ramalinga Viswanathan Rivas,Bernabé L. Becerra,José Naveenraj,Selvaraj RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
description	ABSTRACT Diethyl 2-((4-nitroanilino)methylene)malonate [4-NANM-E] is an important molecule owing to its role of precursor in the multistage synthesis of several quinoline derivatives possessing biological activities such as antiviral, immunosuppressive, anticancer and photoprotector. This molecule is usually synthesized by a nucleophilic vinyl substitution (SNV) between 4-nitroaniline and diethylethoxymethylene malonate (EMA). Although several procedures are available to synthesize 4-NANM-E in liquid phase, more convenient method is necessary to synthesize in less reaction time and at room temperature. In this study, it is demonstrated that equimolar amounts of EMA and 4-nitroaniline dissolved in alcoholic KOH react within a few seconds at room temperature to produce 4-NANM-E which is purified by simple filtration after acidification with aqueous HCl and washing with alcohol. The reaction has the yield varying at the range 45-53% when it occurs in ethanol, 2-propanol, 2-butanol or 2-pentanol. Therefore, this synthesis method is an excellent alternative to produce 4-NANM-E on an industrial scale.
author	Valle,Hernán Mangalaraja,Ramalinga Viswanathan Rivas,Bernabé L. Becerra,José Naveenraj,Selvaraj
author_facet	Valle,Hernán Mangalaraja,Ramalinga Viswanathan Rivas,Bernabé L. Becerra,José Naveenraj,Selvaraj
author_sort	Valle,Hernán
title	RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
title_short	RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
title_full	RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
title_fullStr	RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
title_full_unstemmed	RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE
title_sort	rapid room temperature liquid phase synthesis of diethyl 2-((4-nitroanilino) methylene)malonate
publisher	Sociedad Chilena de Química
publishDate	2018
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000304098
work_keys_str_mv	AT vallehernan rapidroomtemperatureliquidphasesynthesisofdiethyl24nitroanilinomethylenemalonate AT mangalarajaramalingaviswanathan rapidroomtemperatureliquidphasesynthesisofdiethyl24nitroanilinomethylenemalonate AT rivasbernabel rapidroomtemperatureliquidphasesynthesisofdiethyl24nitroanilinomethylenemalonate AT becerrajose rapidroomtemperatureliquidphasesynthesisofdiethyl24nitroanilinomethylenemalonate AT naveenrajselvaraj rapidroomtemperatureliquidphasesynthesisofdiethyl24nitroanilinomethylenemalonate
_version_	1714200929226457088

RAPID ROOM TEMPERATURE LIQUID PHASE SYNTHESIS OF DIETHYL 2-((4-NITROANILINO) METHYLENE)MALONATE

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