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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information