【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% |
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 |