Presentation: 2024 ND EPSCoR Annual conference
November 21, 2024, Alerus Center, Grand Forks, North Dakota
Rapid Synthesis of N-[1-(5-bromo-3-pyridyl)ethyl]-N-methylformamide
Tambraye
Trottier
Undergraduate Student
Minot State University
Co-authors: Mikhail Bobylev, PhD, Minot State University; Lioudmila Bobylev, MS, Minot State University
Session
Poster Session B
Poster #37
Background: Recently, we developed a rapid procedure for the Leuckart reaction and successfully applied it for the synthesis of substituted N-(1-phenylethyl)formamides. Specifically, the reaction between 4-bromoacetophenone and N-methylformamide was completed in 75 minutes and produced N-[1-(4-bromophenyl)ethyl]-N-methylformamide with an isolated yield of 90%. The new procedure appeared to be much faster than the traditional Leuckart reaction that is usually completed within 3 to 6 hours. Hypothesis: Replacing acetophenone with acetylpyridine will introduce a more electronegative atom into the aromatic ring. It will reduce the electron density on the carbonyl and make it more reactive towards formamide in the Leuckart reaction, resulting in a shorter reaction time. In this work, the hypothesis was tested in the reaction between 3-acetyl-5-bromopyridine and N-methylformamide. Methods: The reaction was conducted on a 5 mmol scale at 180ºC - 198ºC. Extraction and column chromatography were used for the isolation of the products of the reaction. NMR-spectroscopy and elemental analysis were used to determine the structures of the products. Result: The reaction was completed in 20 minutes and produced N-[1-(5-bromo-3-pyridyl)ethyl]-N-methylformamide in good yield. Conclusion: The results of the reaction support the initial hypothesis that replacing acetophenone with acetylpyridine will accelerate the Leuckart reaction. Support: Research presented in this presentation was supported by NIH grant 8 P20 GM103442-12 from the National Institute of General Medical Sciences and by the National Science Foundation under NSF EPSCoR Track-1 Cooperative Agreement OIA #1946202
The ND-ACES NSF Track-1 cooperative agreement is a federal-state partnership to manage a comprehensive research development plan. ND EPSCoR manages the Track-1 award. Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation. Current funding is provided by the State of North Dakota and NSF EPSCoR Research Infrastructure Improvement Program Track-1 (RII Track-1) Cooperative Agreement Award OIA #1946202.