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【结 构 式】

【分子编号】24715

【品名】7-amino-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

【CA登记号】

【 分 子 式 】C12H11FN2O3

【 分 子 量 】250.2294232

【元素组成】C 57.6% H 4.43% F 7.59% N 11.2% O 19.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The reduction of 4-fluoro-3-nitroaniline (I) with SnCl2.2H20 in concentrated aqueous HCl gives 4 fluoro-m-phenylenediamine (II), which is condensed with diethyl ethoxymethylenemalonate (III) in refluxing ethanol to afford diethyl 4-fluoro-3-aminoanilinomethylenemalonate (IV). The cyclization of (IV) by means of acetic anhydride in diphenyl oxide at 250 C yields ethyl 7-acetamido-4-hydroxy-6-fluoroquinoline-3-carboxylate (V), which is alkyiated with ethyl bromide and NaOH in refluxing ethanol to give 7-amino-6-fluoro-1-ethyl-1,4 dihydro-4-oxoquinoline-3-carboxylic acid (VI). Finally, this compound is condensed with 2,5-dimethoxytetrahydrofuran (VII) in hot acetic acid.

1 Esteve Soler, J. (Provesan SA); 7-(1-Pyrrolyl) derivs. of 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids and 1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids and their use as antimicrobial agents. EP 0134165; FR 2548664; FR 2559484; US 4552882 .
2 Prous, J.; Castaner, J.; Irloxafin. Drugs Fut 1986, 11, 10, 839.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 24710 4-fluoro-3-nitroaniline 364-76-1 C6H5FN2O2 详情 详情
(II) 24711 3-amino-4-fluorophenylamine C6H7FN2 详情 详情
(III) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(IV) 24713 diethyl 2-[(3-amino-4-fluoroanilino)methylene]malonate C14H17FN2O4 详情 详情
(V) 24714 ethyl 7-(acetamido)-6-fluoro-4-hydroxy-3-quinolinecarboxylate C14H13FN2O4 详情 详情
(VI) 24715 7-amino-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C12H11FN2O3 详情 详情
(VII) 12132 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether 696-59-3 C6H12O3 详情 详情
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