Background: Recently, we developed a rapid procedure for synthesis of substituted N-benzyl-N-methylformamides. Interestingly, in the reaction conducted on 3-methoxybenzaldehyde, nearly equal amounts of N,N-di-(3-methoxybenzyl)-N-methylamine and N-(3-methoxybenzyl)-N-methylformamide were produced with the isolated yields of 49.2% and 46.6%, respectively. Hypothesis: The reaction conducted on 2,3,4-trimethoxybenzaldehyde may produce a higher yield of N-(2,3,4-trimethoxybenzyl)-N-methylformamide, if the inductive electron-withdrawing effect of the methoxy groups will prevail. Alternatively, if the electron-donating effect through resonance prevails, the reaction will produce a higher yield of N,N-di-(2,3,4-trimethoxybenzyl)-N-methylamine. Methods: The reaction was conducted on 10 mmol scale at 199.5-200.5 °C. Column chromatography was used for the isolation of the products. NMR-spectroscopy and elemental analysis were used to determine the structures of the products. Results: The reaction was completed in 10 minutes. The isolated yields of N,N-di-(2,3,4-trimethoxybenzyl)-N-methylamine and N-(2,3,4-trimethoxybenzyl)-N-methylformamide were 32.2% and 63.6%, respectively. The ratio of the yields shifted from 1.06:1 to 1:1.98. Conclusions: The results of the reaction indicate that the inductive electron-withdrawing effect of the methoxy groups prevailed. The reaction provides a new method for the synthesis of N-(2,3,4-trimethoxybenzyl)-N-methylformamide and N,N-di-(2,3,4-trimethoxybenzyl)-N-methylamine.

Rapid synthesis of N-(2,3,4-trimethoxybenzyl)-N-methylformamide

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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