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【结 构 式】

【分子编号】31476

【品名】4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione

【CA登记号】

【 分 子 式 】C9H11NO2

【 分 子 量 】165.19188

【元素组成】C 65.44% H 6.71% N 8.48% O 19.37%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The reaction of cyclohexane-1,3-dione (I) with ammonia gives 3-amino-2-cyclohexen-1-one (II), which is cyclized with acrylic acid (III) by heating at 140 C yielding 1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione (IV). The dehydrogenation of (IV) by means of Pd/C in refluxing decaline affords 5-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (V), which is condensed with epichlorohydrin (VI) by means of NaOMe or NaOH in methanol giving 5-(2,3-epoxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one (VII). Finally, this compound is treated with tert-butylamine in methanol.

1 Castaner, J.; Sungurbey, K.; Carteolol. Drugs Fut 1977, 2, 5, 288.
2 Shono, T.; et al.; A new practical synthesis of 5-hydroxy-3,4-dihydrocarbostyril and 5-hydroxycarbostyril. J Org Chem 1981, 46, 3719.
3 Von Winkler, W.; Chemical and analytical data for the pharmaceutically active substance carteolol hydrochloride. Arzneim-Forsch Drug Res 1983, 33, 2a, 279.
4 Mori, H.; Tamura, Y,.; Tominaga, M.; Yoshiaki, S.; Nakagawa, K.; Murakami, N. (Otsuka Pharmaceutical Co., Ltd.); 3,4-Dihydrocarbostyril derivs., their preparation, and pharmaceutical compsns. thereof. DE 2302027; GB 1424571 .
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) 11244 1,3-Cyclohexanedione 504-02-9 C6H8O2 详情 详情
(II) 31475 3-amino-2-cyclohexen-1-one 5220-49-5 C6H9NO 详情 详情
(III) 19139 acrylic acid 79-10-7 C3H4O2 详情 详情
(IV) 31476 4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione C9H11NO2 详情 详情
(V) 31477 5-hydroxy-3,4-dihydro-2(1H)-quinolinone C9H9NO2 详情 详情
(VI) 29648 2-oxiranylmethanol 556-52-5 C3H6O2 详情 详情
(VII) 31478 5-(2-oxiranylmethoxy)-3,4-dihydro-2(1H)-quinolinone C12H13NO3 详情 详情
(VIII) 17895 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine 75-64-9 C4H11N 详情 详情
Extended Information