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【结 构 式】

【分子编号】33628

【品名】ethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate

【CA登记号】

【 分 子 式 】C17H20ClNO2

【 分 子 量 】305.80404

【元素组成】C 66.77% H 6.59% Cl 11.59% N 4.58% O 10.46%

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:(VI)

The condensation of cyclohexenone (I) with diethyl alpha-methylmalonate (II) by means of sodium ethoxide in ethanol gives diethyl alpha-methyl-3-oxocyclohexanemalonate (III), oil b.p.(0.8) = 149-52 C, n(20)(D) = 1.4660, which is hydrolyzed and decarboxylated with refluxing dioxane-HCl to yield alpha-methyl-3-oxocyclohexaneacetic acid (IV), oil, b.p.(0.7) = 164-6 C, n(20)(D) = 1.4794. The condensation of (IV) with 4-chlorophenylhydrazine (A) in acetic acid-water atfords 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic acid (V), m.p. 193-202 C, which is esterified with ethanol-HCl to ethyl 6-chloro-alpha-methyl-1,2,3,4-tetrahydrocarbazole-2-acetate (VI) and aromatized with chloranil (B) in refluxing xylene to give ethyl 6-chloro-alpha-methylcarbazole-2-acetate (VII), m.p. 106.0-7.5 C. Finally, this ester is hydrolyzed with NaOH in refluxing ethanol.

1 Berger, L.; Corraz, A.J.; Carbazoles. ES 417167; ES 442684; ES 442685; US 3896145 .
2 Weetman, D.F.; Castaner, J.; Carprofen. Drugs Fut 1977, 2, 1, 15.
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) 21891 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil 118-75-2 C6Cl4O2 详情 详情
(A) 33345 1-(4-chlorophenyl)hydrazine; 4-Chlorophenylhydrazine 1073-70-7 C6H7ClN2 详情 详情
(I) 26253 2-cyclohexen-1-one;Cyclohex-2-enone;2-cyclohexenone 930-68-7 C6H8O 详情 详情
(II) 30310 diethyl 2-methylmalonate 609-08-5 C8H14O4 详情 详情
(III) 33625 diethyl 2-methyl-2-(3-oxocyclohexyl)malonate C14H22O5 详情 详情
(IV) 33626 2-(3-oxocyclohexyl)propionic acid C9H14O3 详情 详情
(V) 33627 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propionic acid C15H16ClNO2 详情 详情
(VI) 33628 ethyl 2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)propanoate C17H20ClNO2 详情 详情
(VII) 33629 ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate C17H16ClNO2 详情 详情
Extended Information