Studies on ketene and its derivatives-12-The structure of the self-condensation product of acetoacetamide

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  • Studies on Ketene and Its Derivatives. XII. The Structure of the Self-Condensation Product of Acetoacetamide.

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Claisen and Meyer2) reported the pyrolysis of acetoacetamide (I) to afford 2, 4-dimethyl-5-oxo-1, 6-dihydro-3-pyridinecarboxamide (II-a), which, on hydrolysis, was converted to the lutidone carboxylic acid (III-a). We re-tested this reaction and found that 3-acetyl-4-amino-6-methyl-2-pyridone (II-b) is the proper structure for the pyrolyzed product and that 3-acetyl-4-hydroxy-6-methyl-2-pyridone (III-b) is the correct one for the hydrolyzed compound.

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