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【结 构 式】 
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【分子编号】33990 【品名】diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate 【CA登记号】 |
【 分 子 式 】C14H16ClNO6 【 分 子 量 】329.73688 【元素组成】C 51% H 4.89% Cl 10.75% N 4.25% O 29.11% |
合成路线1
该中间体在本合成路线中的序号：(XI)The reaction of 2,4-dichloronitrobenzene (X) with sodium diethyl methylmalonate (B) in DMF to diethyl 2-(4-nitro-3-chlorophenyl)-2-methyl-malonate (XI), b.p. 147-8 C/0.25 mm, followed hydrolysis, decarboxylation and esterification to ethyl 2-(3-chloro-4-nitrophenyl)propionate (XII), b.p. 138-42 C /0.25 mm; which, in turn, was reduced as before to ethyl 2-(3-chloro-4-aminophenyl)propionate hydrochloride (VI). Conversely, the diethyl 2-(4-nitro-3-chlorophenyl)-2-methylmalonate (XI), already obtained before, could be hydrogenated first to diethyl 2-(4-amino-3-chlorophenyl)-2-methylmalonate (XIII), b.p. 180-5 C/0.25 mm, and then hydrolyzed, decarboxylated and esterified again to ethyl 2-(3-chloro-4-aminophenyl)propionate hydrochloride (VI).
| 【1】 Carney, R.W.; et al.; Potent nonsteroidal anti-inflammatory agent, 2-[3-chloro-4-(3-pyrrolin-1-yl)phenyl]propionic acid. Experientia 1973, 29, 8, 938. |
| 【2】 Castaner, J.; Pirprofen. Drugs Fut 1977, 1, 1, 23. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 32186 | (E)-1,4-dichloro-2-butene | 110-57-6 | C4H6Cl2 | 详情 | 详情 |
| (B) | 33989 | C8H13NaO4 | 详情 | 详情 | ||
| (VI) | 33987 | ethyl 2-(4-amino-3-chlorophenyl)propanoate | C11H14ClNO2 | 详情 | 详情 | |
| (VII) | 33988 | ethyl 2-[3-chloro-4-(2,5-dihydro-1H-pyrrol-1-yl)phenyl]propanoate | C15H18ClNO2 | 详情 | 详情 | |
| (X) | 21787 | 2,4-dichloro-1-nitrobenzene | 611-06-3 | C6H3Cl2NO2 | 详情 | 详情 |
| (XI) | 33990 | diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate | C14H16ClNO6 | 详情 | 详情 | |
| (XII) | 33991 | ethyl 2-(3-chloro-4-nitrophenyl)propanoate | C11H12ClNO4 | 详情 | 详情 | |
| (XIII) | 33992 | diethyl 2-(4-amino-3-chlorophenyl)-2-methylmalonate | C14H18ClNO4 | 详情 | 详情 |