Hexane → Ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxyl ate

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Reaction Steps

Ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methyl-5-nitro-4-oxoquinoline-3-carboxylate (2.50 g, 7.10 mmol) was dissolved in acetonitrile (20 ml), and after adding a 5% palladium carbon catalyst (water content: 50%, 1.0 g) thereto, it was stirred at room temperature for 20 hours under a hydrogen atmosphere at atmospheric pressure. After removing the catalyst by filtering (methanol washing), the filtrate was concentrated under a reduced pressure, and the residue obtained was dissolved in ethyl acetate (10 ml) and heated under reflux for 30 minutes. n-hexane (10 ml) was then added, and after performing heated refluxing for 30 minutes, there action solution was allowed to stand under room temperature. The precipitated crystals were then filtered out, washed with a 1:1 mixed solution of n-hexane:ethyl acetate and dried under a reduced pressure at 60° C. for 16 hours. 869 mg (38%) of the title compound was thereby obtained as a yellow powder.

Provenance & Evidence