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【结 构 式】 
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【分子编号】39063 【品名】8-hydroxy-5-nitro-3,4-dihydro-2(1H)-quinolinone 【CA登记号】 |
【 分 子 式 】C9H8N2O4 【 分 子 量 】208.1736 【元素组成】C 51.93% H 3.87% N 13.46% O 30.74% |
合成路线1
该中间体在本合成路线中的序号：(II)The nitration of 8-hydroxy-3,4-dihydrocarbostyril (I) with HNO3 in acetic acid-acetic anhydride gives 5-nitro-8-hydroxy-3,4-dihydrocarbostyril (II), which is reduced with SnCl2 in concentrated HCl yielding 5-amino-8-hydroxy-3,4-dihydrocarbostyril (III). The oxidation of (III) with FeCl3 in aqueous HCl affords 5,8-dioxo-3,4,5,8-tetrahydrocarbostyril (IV), which by treatment with SO2 in water is converted into 5,8-dihydroxy-3,4-dihydrocarbostyril (V). The treatment of (V) with benzyl chloride (A) and potassium carbonate in acetone gives 5-hydroxy-8-benzyloxy-3,4-dihydrocarbostyril (VII), which by reaction with epichlorohydrin (B) by means of piperidine affords 8-benzyloxy-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril (VII). The opening of the epoxide ring of (VII) with tert-butylamine (C) in methanol yields 8-benzyloxy-5-(3-tert-butylamino-2-hydroxypropoxy)-3,4-dihydrocarbostyril (VIII) (1,2), which is finally hydrogenated with H2 over Pd/C.
| 【1】 Castaner, J.; Blancafort, P.; Serradell, M.N.; 8-Hydroxycarteolol. Drugs Fut 1980, 5, 2, 78. |
| 【2】 Uchida, M.; et al.; Synthesis of 5-(3-tert-butylamino-2-hydroxypropxy)-8-3,4-dihydrocarbostyril hydochloride and its beta-adrenergic blocking agent. Yakugaku Zasshi 1976, 96, 5, 571-577. |
| 【3】 Nakagawa, K.; et al.; US 4072683 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (A) | 19171 | 1-(Chloromethyl)benzene; Benzyl chloride | 100-44-7 | C7H7Cl | 详情 | 详情 |
| (I) | 39062 | 8-hydroxy-3,4-dihydro-2(1H)-quinolinone | 22246-18-0 | C9H9NO2 | 详情 | 详情 |
| (II) | 39063 | 8-hydroxy-5-nitro-3,4-dihydro-2(1H)-quinolinone | C9H8N2O4 | 详情 | 详情 | |
| (III) | 39064 | 5-amino-8-hydroxy-3,4-dihydro-2(1H)-quinolinone | C9H10N2O2 | 详情 | 详情 | |
| (IV) | 39065 | 3,4,4a,8a-tetrahydro-2,5,8(1H)-quinolinetrione | C9H9NO3 | 详情 | 详情 | |
| (V) | 39066 | 5,8-dihydroxy-3,4-dihydro-2(1H)-quinolinone | C9H9NO3 | 详情 | 详情 | |
| (VI) | 39067 | 8-(benzyloxy)-5-hydroxy-3,4-dihydro-2(1H)-quinolinone | C16H15NO3 | 详情 | 详情 | |
| (VII) | 39068 | 8-(benzyloxy)-5-(2-oxiranylmethoxy)-3,4-dihydro-2(1H)-quinolinone | C19H19NO4 | 详情 | 详情 | |
| (VIII) | 39069 | 8-(benzyloxy)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2(1H)-quinolinone | C23H30N2O4 | 详情 | 详情 | |
| (C) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |