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

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Santos Nascimento, Lillian Ferreira [UNIFESP]
Santos Fernandes, Joao Paulo [UNIFESP]
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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.
Green Processing And Synthesis. Berlin, v. 6, n. 2, p. 203-209, 2017.