Carprofen, Ro-20-5720, C-5720, Rimadyl, Imadyl

卡洛芬Chemical Name: (?-6-Chloro-alpha-methylcarbazole-2-acetic acid; (?-2-(6-Chlorocarbazol-2-yl)propanoic acid
CAS No. 53716-49-7
项目整合开发状态: Launched-1981
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The condensation of cyclohexenone (I) with diethyl alpha-methylmalonate (II) by means of sodium ethoxide in ethanol gives diethyl alpha-methyl-3-oxocyclohexanemalonate (III),oil b.p.(0.8) = 149-52 C,n(20)(D) = 1.4660,which is hydrolyzed and decarboxylated with refluxing dioxane-HCl to yield alpha-methyl-3-oxocyclohexaneacetic acid (IV),oil,b.p.(0.7) = 164-6 C,n(20)(D) = 1.4794.The condensation of (IV) with 4-chlorophenylhydrazine (A) in acetic acid-water atfords 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid (V),m.p.193-202 C,which is esterified with ethanol-HCl to ethyl 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetate (VI) and aromatized with chloranil (B) in refluxing xylene to give ethyl 6-chloro-alpha-methylcarbazole-2-acetate (VII),m.p.106.0-7.5 C.Finally,this ester is hydrolyzed with NaOH in refluxing ethanol.