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【结 构 式】 
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【分子编号】32961 【品名】3-chloro-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile 【CA登记号】 |
【 分 子 式 】C16H9ClN2O2 【 分 子 量 】296.71244 【元素组成】C 64.77% H 3.06% Cl 11.95% N 9.44% O 10.78% |
合成路线1
该中间体在本合成路线中的序号：(IV)Benzylic bromination of 3-chloro-4-methylbenzonitrile (I) by means of N-bromosuccinimide and azobis(isobutyronitrile) provided bromide (II). Subsequent displacement of the bromine atom of (III) by potassium phthalimide (III) afforded the N-substituted phthalimide (IV), which was then deprotected with ethanolic hydrazine to furnish the primary amine (V).
| 【1】 Antane, M.M.; Herbst, D.R.; McFarlane, G.R.; Gundersen, E.G.; Hirth, B.H.; Quagliato, D.A.; Graceffa, R.F.; Butera, J.A.; Gilbert, A.M. (American Home Products Corp.); Substd. N-arylmethylamino derivs. of cyclobutene-3, 4-diones. US 5763474; US 5780505; WO 9802413 . |
| 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) | 32959 | 3-chloro-4-methylbenzonitrile | C8H6ClN | 详情 | 详情 | |
| (II) | 32960 | 4-(bromomethyl)-3-chlorobenzonitrile | C8H5BrClN | 详情 | 详情 | |
| (III) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (IV) | 32961 | 3-chloro-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile | C16H9ClN2O2 | 详情 | 详情 | |
| (V) | 32962 | 4-(aminomethyl)-3-chlorobenzonitrile | C8H7ClN2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Benzylic bromination of 3-chloro-4-methylbenzonitrile (I) by means of N-bromosuccinimide and azobis(isobutyronitrile) provided bromide (II). Subsequent displacement of the bromine atom of (II) by potassium phthalimide (III) afforded the N-substituted phthalimide (IV), which was then deprotected with ethanolic hydrazine to furnish the primary amine (V).
| 【1】 Antane, M.M.; Herbst, D.R.; McFarlane, G.R.; Gundersen, E.G.; Hirth, B.H.; Quagliato, D.A.; Graceffa, R.F.; Butera, J.A.; Gilbert, A.M. (American Home Products Corp.); Substd. N-arylmethylamino derivs. of cyclobutene-3, 4-diones. US 5763474; US 5780505; WO 9802413 . |
| 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) | 32959 | 3-chloro-4-methylbenzonitrile | C8H6ClN | 详情 | 详情 | |
| (II) | 32960 | 4-(bromomethyl)-3-chlorobenzonitrile | C8H5BrClN | 详情 | 详情 | |
| (III) | 27980 | Diisopropyl (diisopropoxyphosphoryl)methylphosphonate; Tetraisopropyl methylenediphosphonate | 1660-95-3 | C13H30O6P2 | 详情 | 详情 |
| (IV) | 32961 | 3-chloro-4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile | C16H9ClN2O2 | 详情 | 详情 | |
| (V) | 32962 | 4-(aminomethyl)-3-chlorobenzonitrile | C8H7ClN2 | 详情 | 详情 |