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acetyl protection of the amino group at position C6 gives 3-fluoro-6-amino-2-(4-ethoxycar-bonylpiperazinyl)pyridine (33.2.22). The resulting amine (33.2.22) is reacted with ethyl ethoxymethylenmalonate, which results in the formation of a derivative of aminomethylenmalonic ester, which upon heating gives the ethyl ester of 6-fluoro-1,4-dihydro-4-oxo-7-(4-ethoxycarbonyl-1-piperazinyl)-1,8-naphthiridin-3-carboxylic acid (33.2.23). Alkylating this with ethyl iodide followed by hydrolysis of the two carboethoxy groups gives enoxacin [79-82].

1.NH3 C5h11 no2

+ C2H5OOC

CK NH

1.NH3 C5h11 no2

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