Pefloxacin, RB 1589, EU 5306, Peflacin, Peflacine
培氟沙星Chemical Name: 6-Fluoro-7-(4-methylpiperazin-1-yl)-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
CAS No. 70458-92-3
项目整合开发状态: Launched-1985
项目研究机构: Aventis Pharma (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Pefloxacin mesylate
文献作者:Bellon,A.
参考来源:Drugs Fut 1982,7(9),646
📄 详细内容
合成路线: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.
参考文献标题:Microbiologie: Sur un nouvel antibact閞ien de synth鑣e: lcid?閠hyl-2-fluoro-6-(m閠hyl-4-piperazinyl-1)-oxo-4-dihydro-1,4-quinol閕ne-3-carboxylique (1589 RB)
文献作者:Pesson,M.; Montay,G.; Goueffon,Y.; Roquet,F.
参考来源:CR Acad Sci Par韘 1981,292
产品链接: CAS No. 70458-92-3››