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【结 构 式】 
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【分子编号】29090 【品名】4-chloro-1H-indole-2,3-dione 【CA登记号】 |
【 分 子 式 】C8H4ClNO2 【 分 子 量 】181.578 【元素组成】C 52.92% H 2.22% Cl 19.52% N 7.71% O 17.62% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The reaction of 3-chloroaniline (X) with choral hydrate (XI) and hydroxylamine gives isonitroso-3-chloroacetanilide (XII), which is cyclized by means of H2SO4 to 4-chloroisatin (XIII). Chlorination of (XIII) with SO2Cl2 affords 4,5-dichloroisatin (XIV), which is oxidized with H2O2 yielding 5,6-dichloroanthranilic acid (XV). The reduction of (XV) with borane in THF gives 6-amino-2,3-dichlorobenzyl alcohol (XVI), which by reaction with SOCl2 in benzene is converted to 6-amino-2,3-dichlorobenzyl chloride (XVII). This compound is condensed with ethyl glycinate (XVIII) by means of triethylamine in refluxing methylene chloride to give ethyl N-(6-amino-2,3-dichlorobenzyl)glycinate (VII), which is cyclized with cyanogen bromide (VIII) in toluene affording ethyl 5,6-dichloro-3,4-dihydro-2-(1H)-iminoquinazoline-3-acetate (IX). Finally, this compound is submitted to a new cyclization by means of triethylamine in refluxing ethanol.
| 【1】 Jenks, T.A.; Beverung, W.N.Jr.; Partyka, R.A. (Bristol-Myers Squibb Co.); Preparation of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-one. CA 1137474 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 29087 | ethyl 2-[(6-amino-2,3-dichlorobenzyl)amino]acetate | C11H14Cl2N2O2 | 详情 | 详情 | |
| (VIII) | 28017 | cyanic bromide；cyanogen bromide | 506-68-3 | CBrN | 详情 | 详情 |
| (IX) | 29088 | ethyl 2-[5,6-dichloro-2-imino-1,4-dihydro-3(2H)-quinazolinyl]acetate | C12H13Cl2N3O2 | 详情 | 详情 | |
| (X) | 25239 | 3-chloroaniline; 3-chlorophenylamine | 108-42-9 | C6H6ClN | 详情 | 详情 |
| (XI) | 14018 | 2,2,2-Trichloro-1,1-ethanediol; Chloral hydrate | 302-17-0 | C2H3Cl3O2 | 详情 | 详情 |
| (XII) | 29089 | N-(3-chlorophenyl)-2-(hydroxyimino)acetamide | C8H7ClN2O2 | 详情 | 详情 | |
| (XIII) | 29090 | 4-chloro-1H-indole-2,3-dione | C8H4ClNO2 | 详情 | 详情 | |
| (XIV) | 29091 | 4,5-dichloro-1H-indole-2,3-dione | C8H3Cl2NO2 | 详情 | 详情 | |
| (XV) | 29092 | 6-amino-2,3-dichlorobenzoic acid | C7H5Cl2NO2 | 详情 | 详情 | |
| (XVI) | 29093 | (6-amino-2,3-dichlorophenyl)methanol | C7H7Cl2NO | 详情 | 详情 | |
| (XVII) | 29094 | 3,4-dichloro-2-(chloromethyl)aniline | C7H6Cl3N | 详情 | 详情 | |
| (XVIII) | 10309 | ethyl 2-aminoacetate; Glycine ethyl ester | 459-73-4 | C4H9NO2 | 详情 | 详情 |