Amfenac sodium, AHR-5850D, Fenazox, Fenamate
氨芬酸钠 氨芬酸 Chemical Name: 2-Amino-3-benzoylbenzeneacetic acid sodium salt monohydrate
CAS No. 61618-27-7, 51579-82-9 (free acid)
项目整合开发状态: Launched-1985
项目研究机构: Meiji Seika (Originator)
合成路线:The reaction of 1-aminoindolin-2-one (I) with phenylacetone (A) by means of acetic acid in refluxing ethanol gives 1-(alpha-methylphenethylidiene-imino)indolin-2-one (II),which by reaction with refluxing ethanolic hydrogen chloride affords ethyl alpha-(2-methyl-3-phenylindol-7-yl)acetate (III).The ozonolysis of (III) in acetic acid yields ethyl 2-acetamido-3-benzoylphenyl-acetate (IV),which is cyclized by refluxing with HCl in acetic acid to give 7-benzoylindolin-2-one (V).Finally,of the ester (III) with KOH in refluxing water affords the corresponding acid (this compound is hydrolyzed with NaOH in refluxing water).The hydrolysis of the ester (III) with KOH in refluxing water affords the corresponding acid (VI),which can be ozonolyzed as before yielding 2-acetamido-3-benzoylphenylacetic acid (VII).This acid can be cyclized to (V) by refluxing with HCl in acetic acid as before.
📌 参考资料/链接：
参考文献标题:Anti-inflammatory methods using 2-amino-3-(5- and 6-)benzoylphenyl acetic acids,esters and metal salts thereof and the compounds
文献作者:Welstead,W.J.Jr.; Moran,H.W.(A.H.Robins Co.Inc.)
参考来源:CA 1012979; DE 2324768; FR 2184934; GB 1521097; US 4045576
📄 详细内容
合成路线:The reaction of 1-aminoindolin-2-one (I) with phenylacetone (A) by means of acetic acid in refluxing ethanol gives 1-(alpha-methylphenethylidiene-imino)indolin-2-one (II),which by reaction with refluxing ethanolic hydrogen chloride affords ethyl alpha-(2-methyl-3-phenylindol-7-yl)acetate (III).The ozonolysis of (III) in acetic acid yields ethyl 2-acetamido-3-benzoylphenyl-acetate (IV),which is cyclized by refluxing with HCl in acetic acid to give 7-benzoylindolin-2-one (V).Finally,of the ester (III) with KOH in refluxing water affords the corresponding acid (this compound is hydrolyzed with NaOH in refluxing water).The hydrolysis of the ester (III) with KOH in refluxing water affords the corresponding acid (VI),which can be ozonolyzed as before yielding 2-acetamido-3-benzoylphenylacetic acid (VII).This acid can be cyclized to (V) by refluxing with HCl in acetic acid as before.
参考文献标题:Amfenac
文献作者:Hillier,K.; Castar,J.
参考来源:Drugs Fut 1978,3(5),340
产品链接: CAS No. 61618-27-7›› 产品链接: CAS No.51579-82-9››