Factorial study to assess an ultrasonic methodology for the allylation of 4-chloroaniline

Factorial study to assess an ultrasonic methodology for the allylation of 4-chloroaniline

Author Santos Nascimento, Lillian Ferreira Autor UNIFESP Google Scholar
Santos Fernandes, Joao Paulo Autor UNIFESP Google Scholar
Abstract N-allylanilines are important compounds that are used to access several bioactive compounds containing indole and dihydroindole nucleus. However, their preparation through allylation can lead to the undesirable N, N-diallyl byproduct. In this work, the N-allylation of 4-chloroaniline was studied. In order to accelerate the process and maximize the monoallylated: diallylated ratio, we reported two full factorial studies to transpose the conventional synthetic procedure to an ultrasound (US) methodology. The evaluated factors were temperature, quantity of reagents (allyl bromide and K2CO3), reaction time, and methodology (conventional or US). The results showed that US did not change the monoallylated: diallylated ratio, but significantly improved the reaction rate, giving increased average monoallylated and total yields of 11.4% and 18.1%, respectively (p < 0.05). The proposed US methodology gave the same yields and product ratio in a 4-h reaction time than the conventional 24-h procedure, without heating and using only an inexpensive US bath to conduct the reactions.
Keywords factorial design
N-allyl-4-chloroaniline
N-allylation
ultrasonic bath
ultrasound-assisted synthesis
xmlui.dri2xhtml.METS-1.0.item-coverage Berlin
Language English
Sponsor Sao Paulo state agency FAPESP
Brazilian agency CNPq
Grant number FAPESP: 2013/20479-9
CNPq: 455411/2014-0
Date 2017
Published in Green Processing And Synthesis. Berlin, v. 6, n. 2, p. 203-209, 2017.
ISSN 2191-9542 (Sherpa/Romeo, impact factor)
Publisher Walter De Gruyter Gmbh
Extent 203-209
Origin http://dx.doi.org/10.1515/gps-2016-0122
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000403508700008
URI https://repositorio.unifesp.br/handle/11600/54783

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