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【结 构 式】 
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【分子编号】39072 【品名】8-hydroxy-2(1H)-quinolinone 【CA登记号】15450-76-7 |
【 分 子 式 】C9H7NO2 【 分 子 量 】161.16012 【元素组成】C 67.08% H 4.38% N 8.69% O 19.86% |
合成路线1
该中间体在本合成路线中的序号：(I)The Friedel-Crafts condensation of 8-hydroxycarbostyril (I) with 2-bromobutyryl chloride by means of AlCl3 in refluxing CS2 gives 5-(2-bromobutyryl)-8-hydroxycarbostyril (II), which by reaction with isopropylamine in isopropanol affords 5-(2-isopropylaminobutyryl)-8-hydroxycarbostyril (III). Finally, this compound is reduced with NaBH4 in methanol.
| 【1】 Nakagawa, K.; et al.; Dérivés de 5-(1-hydroxy-2-amino substitué)alkyl-8-carbostyryle substitué et de 5-(1-hydroxy-2-amino substitué)alkyl-8-(3,4-dihydro)carbostyryle substitué et leur procédé de préparation. BE 0823841; JP 50095279 . |
| 【2】 Yoshizaki, S.; et al.; Sympathomimetic amines having a carbostyril nucleus. J Med Chem 1976, 19, 9, 35-45. |
| 【3】 Castaner, J.; Weetman, D.F.; Procaterol. Drugs Fut 1978, 3, 2, 135. |
| 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) | 39072 | 8-hydroxy-2(1H)-quinolinone | 15450-76-7 | C9H7NO2 | 详情 | 详情 |
| (II) | 39781 | 2-bromobutanoyl chloride | 22118-12-3 | C4H6BrClO | 详情 | 详情 |
| (III) | 39782 | 5-(2-bromobutanoyl)-8-hydroxy-2(1H)-quinolinone | C13H12BrNO3 | 详情 | 详情 | |
| (IV) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
| (V) | 39783 | 8-hydroxy-5-[2-(isopropylamino)butanoyl]-2(1H)-quinolinone | C16H20N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XII)The dihydroxy compound (V) can also be obtained as follows: the nitration of 8-hydroxycarbostyril (XII) with HNO3 in acetic acid-acetic anhydride gives 5-nitro-8-hydroxycarbostyril (XIII), which is reduced with SnCl2 yielding 5-amino-8-hydroxycarbostyril (XIV). The oxidation of (XIV) with FeCl3 affords 5,8-dioxo-5,8-dihydrocarbostyril (XV), which is reduced with SO2 giving 5,8-dihydroxycarbostyril (XVI). Finally, this compound is reduced with H2 over Pd/C. The 5-amino-8-hydroxy compound (XIV) can also be obtained by nitrosation of (XII) with NaNO2 in acetic acid acetic anhydride to give 5-nitroso-8-acetoxycarbostyril (XVII), which is then reduced with SnCl2 in concentrated HCl.
| 【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. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 39066 | 5,8-dihydroxy-3,4-dihydro-2(1H)-quinolinone | C9H9NO3 | 详情 | 详情 | |
| (XII) | 39072 | 8-hydroxy-2(1H)-quinolinone | 15450-76-7 | C9H7NO2 | 详情 | 详情 |
| (XIII) | 39073 | 8-hydroxy-5-nitro-2(1H)-quinolinone | C9H6N2O4 | 详情 | 详情 | |
| (XIV) | 39074 | 5-amino-8-hydroxy-4a,5,8,8a-tetrahydro-2(1H)-quinolinone | C9H12N2O2 | 详情 | 详情 | |
| (XV) | 39075 | 4a,8a-dihydro-2,5,8(1H)-quinolinetrione | C9H7NO3 | 详情 | 详情 | |
| (XVI) | 39076 | 5,8-dihydroxy-2(1H)-quinolinone | C9H7NO3 | 详情 | 详情 | |
| (XVII) | 39077 | 5-nitroso-2-oxo-1,2,4a,5,8,8a-hexahydro-8-quinolinyl acetate | C11H12N2O4 | 详情 | 详情 |