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【结 构 式】

【分子编号】57755

【品名】2-(4-methoxyanilino)benzoic acid

【CA登记号】

【 分 子 式 】C14H13NO3

【 分 子 量 】243.26216

【元素组成】C 69.12% H 5.39% N 5.76% O 19.73%

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:(III)

Ullmann condensation between o-chlorobenzoic acid (I) and p-anisidine (II) produces the diphenylamine carboxylic acid (III), which is further cyclized to the 2-methoxyacridone (IV) by heating in polyphosphoric acid. N-Alkylation of acridone (IV) with 1-bromo-4-chlorobutane (V) in the presence of KOH under phase-transfer conditions furnishes the N-(chlorobutyl)acridone (VI). Finally, nucleophilic substitution of the chloro group of (VI) with N-(2-hydroxyethyl)piperazine (VII) gives rise to the title compound.

1 Krishnegowda, G.; et al.; Synthesis and chemical characterization of 2-methoxy-N10-substituted acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells. Bioorg Med Chem 2002, 10, 7, 2367.
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) 10203 o-Chlorobenzoic acid; 2-Chlorobenzoic acid 118-91-2 C7H5ClO2 详情 详情
(II) 10478 p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine 104-94-9 C7H9NO 详情 详情
(III) 57755 2-(4-methoxyanilino)benzoic acid C14H13NO3 详情 详情
(IV) 57756 2-Methoxy-9(10H)-acridone C14H11NO2 详情 详情
(V) 16141 1-bromo-4-chlorobutane 6940-78-9 C4H8BrCl 详情 详情
(VI) 57757 10-(4-chlorobutyl)-2-methoxy-9(10H)-acridinone C18H18ClNO2 详情 详情
(VII) 21893 2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine 103-76-4 C6H14N2O 详情 详情
Extended Information