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【结 构 式】 
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【分子编号】30307 【品名】2-(4-nitrophenyl)acrylic acid 【CA登记号】 |
【 分 子 式 】C9H7NO4 【 分 子 量 】193.15892 【元素组成】C 55.96% H 3.65% N 7.25% O 33.13% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 4-nitrophenylacetic acid (I) with formaldehyde and dimethylamine in water gives 2-(4-nitrophenyl)-3-(dimethylamino)propionic acid (II), which by treatment with refluxing concentrated HCl is converted into 2-(4-nitrophenyl)acrylic acid (III). The esterification of (III) with methanol and p-toluenesulfonic acid yields the corresponding methyl ester (IV), which is reduced with H2 over Pd/C in ethanol to afford methyl 2-(4-aminophenyl)propionate (V). The alkylation of (V) with 2-methylallyl chloride (VI) by means of pyridine in refluxing ethanol gives methyl 2-[4-(2-methylallylamino)phenyl]propionate (VII), which is finally hydrolyzed with NaOH in refluxing methanol.
| 【1】 Dumaitre, B.; et al.; Synthesis of some analgesic and antiinflammatory 4-aminophenylacetic and 4-aminophenylacetic and 2-(4-aminophenyl)propionic acid derivatives. Eur J Med Chem - Chim Ther 1979, 14, 3, 207-214. |
| 【2】 Bouchara, E. (Laboratoires du Dr. E. Bouchara); Nouveau procede de preparation de derives de l'acide phenylacetique. FR 2289180 . |
| 【3】 Serradell, M.N.; Castaner, J.; Alminoprofen. Drugs Fut 1984, 9, 3, 165. |
| 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) | 30305 | 2-(4-nitrophenyl)acetic acid | 104-03-0 | C8H7NO4 | 详情 | 详情 |
| (II) | 30306 | N,N-dimethyl-2-(4-nitrophenyl)-beta-alanine | C11H14N2O4 | 详情 | 详情 | |
| (III) | 30307 | 2-(4-nitrophenyl)acrylic acid | C9H7NO4 | 详情 | 详情 | |
| (IV) | 30308 | methyl 2-(4-nitrophenyl)acrylate | C10H9NO4 | 详情 | 详情 | |
| (V) | 13912 | methyl 2-(4-aminophenyl)propanoate | 39718-97-3 | C10H13NO2 | 详情 | 详情 |
| (VI) | 12127 | 3-Chloro-2-methyl-1-propene; Isobutenyl chloride | 563-47-3 | C4H7Cl | 详情 | 详情 |
| (VII) | 30309 | methyl 2-[4-[(2-methyl-2-propenyl)amino]phenyl]propanoate | C14H19NO2 | 详情 | 详情 |