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【结 构 式】 
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【分子编号】21100 【品名】(2-nitrophenyl)(phenyl)methanone 【CA登记号】2243-79-0 |
【 分 子 式 】C13H9NO3 【 分 子 量 】227.2194 【元素组成】C 68.72% H 3.99% N 6.16% O 21.12% |
合成路线1
该中间体在本合成路线中的序号：(III)This compound can be prepared by two related ways: 1) The reaction of 2-nitrobenzoic acid (I) with PCl5 at 50 C gives the corresponding acyl chloride (II), which by a Friedel-Craft's condensation with benzene and AlCl3 yields 2-nitrobenzophenone (III). The reduction of (III) with H2 over Pd/C in ethanol affords 2-aminobenzophenone (IV), which is acylated with acetic anhydride sodium acetate to give 2-acetamidobenzophenone (V). The cyclization of (V) by means of sodium methoxide in refluxing ethanol yields 4-phenylquinoline-2(1H)-one (VI), which by reaction with SOCl2-DMF in hot CHCl3 is converted to 2-chloro-4-phenylquinoline (VII). Finally, this compound is condensed with N-ethylpiperazine (VIII) at 130 C. 2) Quinoline (VII) is condensed with piperazine (IX) as before to give 4-phenyl-2-(1-piperazinyl)quinoline (X), which is finally alkylated with ethyl iodide and sodium carbonate in refluxing butanone.
| 【1】 Uno, H.; Nagai, Y.; Karasawa, T.; Furukawa, K. (Dainippon Pharm. Co.; Ltd.); 2-(4-Ethyl-1-piperazinyl)-4-phenylquinoline and its salts with acids, process for their preparation and their use as antidepressant agents. DE 2912414 . |
| 【2】 Uno, H.; Nagai, Y.; Hino, K.; Kawashima, K.; Oka, M.; Matsumoto, J.; A novel class of antiulcer agents. 4-Phenyl-2-(1-piperazinyl)quinolines. Chem Pharm Bull 1989, 37, 1, 110. |
| 【3】 Prous, J.; Castaner, J.; AD-2646. Drugs Fut 1989, 14, 8, 735. |
| 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) | 20951 | 2-nitrobenzoic acid；o-Nitrobenzoic acid | 552-16-9 | C7H5NO4 | 详情 | 详情 |
| (II) | 21099 | o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride | 610-14-0 | C7H4ClNO3 | 详情 | 详情 |
| (III) | 21100 | (2-nitrophenyl)(phenyl)methanone | 2243-79-0 | C13H9NO3 | 详情 | 详情 |
| (IV) | 21101 | (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone | 2835-77-0 | C13H11NO | 详情 | 详情 |
| (V) | 21102 | N-(2-benzoylphenyl)acetamide | 85-99-4 | C15H13NO2 | 详情 | 详情 |
| (VI) | 21103 | 4-phenyl-2(1H)-quinolinone | C15H11NO | 详情 | 详情 | |
| (VII) | 21104 | 2-chloro-4-phenylquinoline | C15H10ClN | 详情 | 详情 | |
| (VIII) | 14213 | N-Ethylpiperazine; 1-Ethylpiperazine | 5308-25-8 | C6H14N2 | 详情 | 详情 |
| (IX) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (X) | 21107 | 4-phenyl-2-(1-piperazinyl)quinoline | C19H19N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)
| 【1】 Moran HW. 1981. 2-Amino-3-[hydroxy (phenyl)-methyl] phenylacetic acids, esters and amides. FR 2470671 |
| 【2】 Walsh DA.1981. 2-Amino-3-benzoyl-phenylacetamiDErivatives, pharmaceutical compositions containing them and process for their preparation. DE 3035688（本专利为Wyeth consumerhealthcare所有） |
| 【3】 Walsh DA. 1990. Antiinflammatory agents.4.Syntheses and biological evaluation of potential prodrugs of 2-amino-3-benzoylbenzeneacetic acid and 2-amincr3-(4-chlorobenzoyl) benzeneacetic acid. J Med Chem,33 (8): 2296～2304 |
| 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) | 20951 | 2-nitrobenzoic acid；o-Nitrobenzoic acid | 552-16-9 | C7H5NO4 | 详情 | 详情 |
| (II) | 21099 | o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride | 610-14-0 | C7H4ClNO3 | 详情 | 详情 |
| (III) | 21100 | (2-nitrophenyl)(phenyl)methanone | 2243-79-0 | C13H9NO3 | 详情 | 详情 |
| (IV) | 21101 | (2-aminophenyl)(phenyl)methanone; 2-Aminobenzophenone | 2835-77-0 | C13H11NO | 详情 | 详情 |
| (V) | 66542 | Acetamide,2-(methylthio)-;(Methylthio)acetamide;2-(Methylthio)acetamide | 22551-24-2 | C3H7NOS | 详情 | 详情 |
| (VI) | 66543 | 2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetamide;2-amino-3-benzoly-a-methylthio-phenylacetamide;2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetamide | 78281-61-5 | C16H16N2O2S | 详情 | 详情 |