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Synthesis 1988; 1988(6): 479-480
DOI: 10.1055/s-1988-27614
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An Easy and Convenient Synthesis of 6-Methyl-4(1H )-pyridone-3-carboxylic Acid

Martin Mittelbach*
  • *Institute for Organic Chemistry, Karl Franzens University of Graz, Heinrichstraße 28, A-8010 Graz, Austria
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Publication Date:
20 August 2002 (online)

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A new and easy synthesis of 6-methyl-4-(1H)-pyridone-3-carboxylic acid (5), an important component of broad spectrum cephalosporins, is described. It starts from the readily available ethyl 4-hydroxy-6-methyl-2(1H)-pyridone-3-carboxylate (1), which is treated with phosphoryl chloride to give ethyl 2,4-dichloro-6-methylpyridine-3-carboxylate (2).Selective substitution of the chlorine in 4-position with alkoxide ion leads to the 4-alkoxypyridine derivatives 3. Hydrogenolysis of 3 affords ethyl 4-alkoxy-6-methyl-pyridine-3-carboxylates 4; which are hydrolysed to 5 in one step.

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