【结 构 式】 |
【分子编号】34142 【品名】1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-1-ethanone 【CA登记号】484-51-5 |
【 分 子 式 】C12H12O5 【 分 子 量 】236.22428 【元素组成】C 61.01% H 5.12% O 33.86% |
合成路线1
该中间体在本合成路线中的序号:(I)The reaction of khellinone (I) with hydroxylamine in refluxing ethanol gives the corresponding oxime (II), which undergoes the Beckmann rearrangement in a saturated solution of gaseous HCl in acetic acid to afford the acetamido compound (III). Treatment of (III) with gaseous HCl in ethanol under reflux yields an aminophenol (VII), which is first reacted with methyl isocyanate (IX) in chloroform, then O-alkylated by pyrrolidinoethyl chloride (IV) in refluxing acetonitrile in the presence of K2CO3 to give carocainide as the free base. Alternatively, (III) can be alkylated by pyrrolidinoethyl chloride (IV), then refluxed in aqueous 2N HCl and the resulting amino compound (VI) reacted with methyl isocyanate (IX) in dry toluene. The hydrochloride can be prepared by treatment of the free base with HCl in methylene chloride-chlorotene.
【1】 Ancher, J.F.; Carocainide Hydrochloride. Drugs Fut 1984, 9, 6, 410. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 34142 | 1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-1-ethanone | 484-51-5 | C12H12O5 | 详情 | 详情 |
(II) | 34143 | 1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-1-ethanone oxime | C12H13NO5 | 详情 | 详情 | |
(III) | 34144 | N-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)acetamide | C12H13NO5 | 详情 | 详情 | |
(IV) | 11019 | (Methylimino)(oxo)methane; methyl isocyanate | C2H3NO | 详情 | 详情 | |
(V) | 34145 | N-[4,7-dimethoxy-6-[2-(1-pyrrolidinyl)ethoxy]-1-benzofuran-5-yl]acetamide | C18H24N2O5 | 详情 | 详情 | |
(VI) | 34146 | 4,7-dimethoxy-6-[2-(1-pyrrolidinyl)ethoxy]-1-benzofuran-5-ylamine; 4,7-dimethoxy-6-[2-(1-pyrrolidinyl)ethoxy]-1-benzofuran-5-amine | C16H22N2O4 | 详情 | 详情 | |
(VII) | 34147 | 5-amino-4,7-dimethoxy-1-benzofuran-6-ol | C10H11NO4 | 详情 | 详情 | |
(VIII) | 34148 | N-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)-N'-methylurea | C12H14N2O5 | 详情 | 详情 | |
(IX) | 33922 | 1-(2-Chloroethyl)pyrrolidine; N-(2-Chloroethyl)pyrrolidine | C6H12ClN | 详情 | 详情 |