Revisiting Dimerization of Acetoacetamide Leading to 4,6-Dimethyl-2-pyridone-5-carboxamide

Sho Hirai; Haruyasu Asahara; Ryuichi Sugimoto; Kazuhiko Saigo; Nagatoshi Nishiwaki

doi:10.5650/jos.ess14004

Chemistry and Organic Synthesis

Revisiting Dimerization of Acetoacetamide Leading to 4,6-Dimethyl-2-pyridone-5-carboxamide

Sho Hirai, Haruyasu Asahara, Ryuichi Sugimoto, Kazuhiko Saigo, Nagatoshi Nishiwaki

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Keywords: dimerization, acetoacetamide, functionalized pyridone, active methylene compound, self-catalyst

JOURNAL FREE ACCESS

2014 Volume 63 Issue 9 Pages 939-942

DOI https://doi.org/10.5650/jos.ess14004

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Abstract

A commercially purchased acetoacetamide was found to dimerize during storage for several months to afford 4,6-dimethyl-2-pyridone-5-carboxamide. We successfully achieved the quantitative dimerization of acetoacetamide by using an acid catalyst. It was also found that the pyridone formed served as a self-catalyst of the dimerization.

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