N-(4-chlorobenzyl)formamide is an important intermediate in the synthesis of medicinally active compounds.  Recently, we developed an accelerated procedure for the synthesis of formamides and successfully used it for the synthesis N-(4-chlorobenzyl)-formamide.  In this work, the newly developed reaction was investigated for the purpose of isolation and investigation of the reaction by-products.  Column chromatography was used for the isolation of the products of the reaction.  NMR and MS spectra and elemental analysis were used to determine the structure of the products.  The reaction was completed in 1 minute and produced N-(4-chlorobenzyl)-formamide in good yield.  Three byproducts were isolated and their structures were determined.  The results will help to better understand the mechanism of the Leuckart reaction.  The project is supported by NIH grant P20 RR016741 from the NCRR and by the Great Plains Center for Community Research and Service as funded by the US Department of Education Grant Award P1 16Z100151

Byproducts in the rapid synthesis of N-(4-chlorobenzyl)formamide

244th National Meeting (2012)

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