a-Photodecarboxylation of Phthaloyl Glycine
Submitted by: Sam Josland and Michael Oelgemoller
James Cook University, College of Science, Technology and Engineering, Townsville, QLD 4811, Australia
Abstract
This application note illustrates the use of the Vapourtec UV-150 photochemical reactor for the conversion of phthaloyl glycine to N-methylphthalimide. The transformation has been systematically optimized in terms of reagent concentration and residence time. The optimized procedure was subsequently performed on large-scale, achieving a productivity of 1.15 g of product per hour (or 27.6 g per day). The reactor enabled continuous photochemistry in an easy-to-use, safe and efficient manner.
The photochemistry of phthalimides has been studied in detail over the last decades and is thus well understood.3 Semi-technical scale reactions of selected transformations in batch using a 308 nm excimer light source have also been reported. 4 The α-photodecarboxylation (-CO2H/-H exchange) of phthaloyl glycine has been chosen as a model reaction for this application note. The reaction offers a mild access to mono-deuterated amines.5 As data is readily available for the same reaction in a conventional Rayonet chamber and an early μ-reactor,6 the efficiency of the UV-150 reactor can be demonstrated by comparison.
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