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Carteolol hydrochloride, OPC-1085, Abbott-43326, Arteolol, Mikelan, Carteol, Teoptic, Arteoptic, Ocupress, Cartrol

盐酸卡替洛尔 卡替洛尔 Chemical Name: 5-[3-(1,1-Dimethylethylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-quinolinone hydrochloride
CAS No. 51781-21-6, 51781-06-7 (free base)
项目整合开发状态: Launched-1982
项目研究机构: Otsuka (Not Determined), Chauvin (Licensee), Lacer (Licensee), Novartis (Licensee)
合成路线:The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II),which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV).The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V),which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII).Finally,this compound is treated with tert-butylamine in methanol.
📌 参考资料/链接:
参考文献标题:3,4-Dihydrocarbostyril derivs.,their preparation,and pharmaceutical compsns.thereof
文献作者:Mori,H.; Tamura,Y,.; Tominaga,M.; Yoshiaki,S.; Nakagawa,K.; Murakami,N.(Otsuka Pharmaceutical Co.,Ltd.)
参考来源:DE 2302027; GB 1424571

📄 详细内容


合成路线:The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II),which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV).The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V),which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII).Finally,this compound is treated with tert-butylamine in methanol.

参考文献标题:A new practical synthesis of 5-hydroxy-3,4-dihydrocarbostyril and 5-hydroxycarbostyril
文献作者:Shono,T.; et al.
参考来源:J Org Chem 1981,463719


合成路线:The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II),which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV).The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V),which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII).Finally,this compound is treated with tert-butylamine in methanol.

参考文献标题:Chemical and analytical data for the pharmaceutically active substance carteolol hydrochloride
文献作者:Von Winkler,W.
参考来源:Arzneim-Forsch Drug Res 1983,33(2a),279


合成路线:The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II),which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV).The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V),which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII).Finally,this compound is treated with tert-butylamine in methanol.
参考文献标题:Carteolol
文献作者:Castar,J.; Sungurbey,K.
参考来源:Drugs Fut 1977,2(5),288


产品链接: CAS No. 51781-21-6››

产品链接: CAS No.51781-06-7››