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【结 构 式】 
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【分子编号】61287 【品名】5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-benzo[g]indole-2,3-dione 【CA登记号】 |
【 分 子 式 】C18H14ClNO2 【 分 子 量 】311.7674 【元素组成】C 69.35% H 4.53% Cl 11.37% N 4.49% O 10.26% |
合成路线1
该中间体在本合成路线中的序号：(VII)1-Amino-5,6,7,8-tetrahydronaphthalene (I) is protected as the corresponding acetamide (II) by treatment with Ac2O in the presence of NaOAc. Bromination of (II) with bromine in trifluoroacetic acid leads to (III). Then, Suzuki coupling between aryl bromide (III) and 4-chlorophenylboronic acid (IV) furnishes the aryl tetrahydronaphthalene (V). Acetamide hydrolysis in (V) under alkaline conditions provides amine (VI). Condensation of (VI) with chloral and hydroxylamine, followed by cyclization in hot methanesulfonic acid generates the isatin derivative (VII). This is finally converted to the title oxime upon treatment with hydroxylamine hydrochloride in ethanol.
| 【1】 Moeller, A.; Peters, D.; Groenborg, M. (NeuroSearch A/S); Isatine derivs. with neurotrophic activity. EP 1255734; US 2003040518; WO 0155110 . |
| 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) | 61282 | 1-Amino-5,6,7,8-tetrahydronaphthalene 5,6,7,8-Tetrahydro-1-naphthylamine 5-Aminotetralin 1-Amino-5,6,7,8-tetrahydronaphthalene, tech. 1-Amino-5,6,7,8-tetrahydronaphthalin 5-Aminotetraline (1-AMINO-5,6,7,8-TETRAHYDRONAPHTHALENE) | 2217-41-6 | C10H13N | 详情 | 详情 |
| (II) | 61283 | N-(5,6,7,8-tetrahydro-1-naphthalenyl)acetamide | C12H15NO | 详情 | 详情 | |
| (III) | 61284 | N-(4-bromo-5,6,7,8-tetrahydro-1-naphthalenyl)acetamide | C12H14BrNO | 详情 | 详情 | |
| (IV) | 17575 | 4-chlorophenylboronic acid | 1679-18-1 | C6H6BClO2 | 详情 | 详情 |
| (V) | 61285 | N-[4-(4-chlorophenyl)-5,6,7,8-tetrahydro-1-naphthalenyl]acetamide | C18H18ClNO | 详情 | 详情 | |
| (VI) | 61286 | 4-(4-chlorophenyl)-5,6,7,8-tetrahydro-1-naphthalenamine; 4-(4-chlorophenyl)-5,6,7,8-tetrahydro-1-naphthalenylamine | C16H16ClN | 详情 | 详情 | |
| (VII) | 61287 | 5-(4-chlorophenyl)-6,7,8,9-tetrahydro-1H-benzo[g]indole-2,3-dione | C18H14ClNO2 | 详情 | 详情 |