Schmidt Reaction of Ketones in DME Solution in a Continuous-Flow Microreactor

Abstract

The Schmidt reaction, the treatment with hydroazoic acid in the presence of a strong acid, converts ketones to amides directly and has been broadly applied in organic synthesis. In this communication, the Schmidt reaction of ketones was carried out in DME solution in a continuous-flow microreactor and gave the amide products. The enclosed small-volume feature of the microreactor made this reaction safe, fast, and costeffective.

A peculiar segmented flow microfluidics for isoquercitrin biosynthesis based on coupling of reaction and separation

“…Andreev examined triethanolamine synthesis from ammonia and ethylene oxide in a continuous flow microchannel reactor over a wide range of temperatures and residence times (Andreev et al, 2015). Chen carried out Schmidt reactions of ketones, conducted in 1, 2-dimethoxyethane (DME) solutions in a continuous-flow microreactor, and produced amide products in a safe, fast, and cost-effective manner (Chen et al, 2014). However, under special conditions, the resultant product may be unstable and lead to a reverse reaction decreasing the final yield.…”

Hydrazoic Acid and Azides

“…The Schmidt rearrangement converts ketones into amides and carboxylic acids into amines, using hydrazoic acid. To circumvent the handling of this dangerous reagent, microreactors have been used [108].…”

Organocatalyzed Beckmann rearrangement of cyclohexanone oxime in a microreactor: Kinetic model and product inhibition

“…Second, higher pressure is easily operated and then the reaction can be proceeded at higher temperature, decreasing the evaporation of TFA. Finally, the small volume usage and easy use of anticorrosive materials in the microreaction system improve the process safety . As a result, the microreactor is quite suitable for the kinetics study of this process because of the better control of reaction conditions and inherent safety characteristics.…”