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【结 构 式】

【分子编号】32074

【品名】Ethyl 7-chloro-6-fluoro-4-hydroxy-1,4-dihydro-3-quinolinecarboxylate

【CA登记号】

【 分 子 式 】C12H11ClFNO3

【 分 子 量 】271.6753832

【元素组成】C 53.05% H 4.08% Cl 13.05% F 6.99% N 5.16% O 17.67%

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:(III)

3-Chloro-4-fluoroaniline (I), condensed by heating at 125 C with diethyl ethoxymethylenemalonate (A), gives diethyl 3-chloro-4-fluoroanilinomethylenemalonate (II). The thermal cyclization of (II) by reflux in A Dowtherm gives ethyl 6-fluoro-7-chloro-4-hydroxyquinoline-3-carboxylate (III), which, alkylated by ethyliodide in DMF with potassium carbonate, leads to ethyl 1-ethyl-6 fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate (IV), purified by recrystallization. The ester (IV), after saponification and acidification, provides the corresponding acid (V). 1-Ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (V), heated to 100 C in pyridine with 1-methylpiperazine (B), leads to 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (VI). The salification of (VI) with methanesulfonic acid provides the salt.

1 Pesson, M.; Montay, G.; Goueffon, Y.; Roquet, F.; Microbiologie: Sur un nouvel antibacterien de synthese:l¡Acide ethyl-2-fluoro-6-(methyl-4-piperazinyl-1)-oxo-4-dihydro-1,4-quinoleine-3-carboxylique (1589 RB). CR Acad Sci Paris 1981, 292.
2 Bellon, A.; Pefloxacin mesylate. Drugs Fut 1982, 7, 9, 646.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(A) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(I) 18688 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline 367-21-5 C6H5ClFN 详情 详情
(II) 32073 Diethyl 2-[[(3-chloro-4-fluorophenyl)imino]methyl]malonate; Diethyl 3-chloro-4-fluoroanilinomethylenemalonate C14H15ClFNO4 详情 详情
(III) 32074 Ethyl 7-chloro-6-fluoro-4-hydroxy-1,4-dihydro-3-quinolinecarboxylate C12H11ClFNO3 详情 详情
(IV) 32075 ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate C14H13ClFNO3 详情 详情
(V) 32076 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid 68077-26-9 C12H9ClFNO3 详情 详情
(VI) 32077 1-ethyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid C17H20FN3O3 详情 详情
Extended Information