Recently, we developed an instant procedure for the Leuckart reaction and successfully applied it for the synthesis of various benzylformamides.  We also reported a successful use of acetamide as an alternative solvent for the Leuckart reaction conducted on sterically hindered ketones.  It was interesting to investigate, if acetamide can be successfully used as a solvent in the rapid synthesis of benzylformamides, for example, N-(4-chlorobenzyl)formamide.  The reaction was conducted on 10 mmol scale at 200�C.  Column chromatography was used for the isolation of the products of the reaction.  NMR-spectroscopy and elemental analysis were used to determine the structure of the products.  The reaction was fully completed in 1 minute and produced N-(4-chlorobenzyl)formamide only as a minor product.  Four other products were also isolated and their structures were determined.  The use of acetamide as a solvent resulted in a substantial shift towards the products of the secondary and tertiary Leuckart reactions.  The results will help to better understand the mechanism of the Leuckart reaction.  The project was supported by NIH grant P20 RR016741 from the NCRR.

Acetamide as a solvent in the rapid synthesis of N-(4-chlorobenzyl)formamide

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.