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【结 构 式】

【分子编号】21231

【品名】ethyl 2-[4-(acetamido)phenyl]acetate

【CA登记号】

【 分 子 式 】C12H15NO3

【 分 子 量 】221.25604

【元素组成】C 65.14% H 6.83% N 6.33% O 21.69%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IX)

The methylation of ethyl 4-nitrophenylacetate (I) with NaH - ICH3 in DMF - toluene to ethyl 2-(4-nitrophenyl)propionate (II), which was reduced with H2 over Pd/C in EtOH - H2O to ethyl 2-(4-aminophenyl)propionate (III) (HCl deriv., m.p. 137-40 C). This product was acetylated with acetic anhydride to ethyl 2-(acetylaminophenyl) propionate (IV), m.p. 88-90 C, which was chlorinated with Cl2 in acetic acid to ethyl 2-(3-chloro-4-acetylaminophenyl)propionate (V), b.p. 155-60 C/0.7 mm; this, in turn, was hydrolyzed with HCl in EtOH to ethyl 2-(3-chloro-4-aminophenyl)propionate hydrochloride (VI), m.p. 164-8 C. The last step being the reaction of the preceding intermediate with cis-1,4-dichloro (or dibromo)-2-butene (A) in DMF and Na2CO3 to ethyl 2-(3-chloro-4-(3-pyrrolinyl)phenyl)propionate (VII), b.p. 128-33 C/0.25 mm; followed by hydrolysis with KOH in EtOH - H2O. The acetylation of ethyl 4-aminophenylacetate (VIII) with acetic anhydride to ethyl 4-acetylaminophenylacetate (IX), m.p. 75-8 C, followed by methylation with ICH3 and Na in liquid NH3 to ethyl 2-(4-acetylaminophenyl)propionate (IV), already obtained.

1 Carney, R.W.J.; de Stevens, G; Tertiary amino phenyl acetic acids. CH 574926; CH 577968; CH 578523; CH 581103; CH 581104; US 3641040 .
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
(I) 33982 ethyl 2-(4-nitrophenyl)acetate 5445-26-1 C10H11NO4 详情 详情
(II) 33983 ethyl 2-(4-nitrophenyl)propanoate C11H13NO4 详情 详情
(III) 33984 ethyl 2-(4-aminophenyl)propanoate C11H15NO2 详情 详情
(IV) 33985 ethyl 2-[4-(acetamido)phenyl]propanoate C13H17NO3 详情 详情
(V) 33986 ethyl 2-[4-(acetamido)-3-chlorophenyl]propanoate C13H16ClNO3 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
(VIII) 21230 ethyl 2-(4-aminophenyl)acetate 5438-70-0 C10H13NO2 详情 详情
(IX) 21231 ethyl 2-[4-(acetamido)phenyl]acetate C12H15NO3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The esterification of 4-aminophenylacetic acid (I) with ethanol - HCl in the usual way gives the ethyl ester (II), which is acylated with acetic anhydride in ethyl acetate yielding ethyl 4-acetaminophenylacetate (III). Finally, this compound is hydrolyzed with aqueous NaOH.

1 Sato, S.; Tsurufuji, M.; Enomoto, H.; Sugiyama, M.; Shibata, Y.; Morita, I.; Munakata, H.; Kobayashi, M.; Wagatsuma, K. (Mitsubishi Chem. Inds. Co.; Ltd.); Immunomodulating agents. DE 3317107; US 4720506 .
2 Prous, J.; Castaner, J.; MS-932. Drugs Fut 1989, 14, 8, 759.
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) 21229 2-(4-Aminophenyl)acetic acid 5345-54-0 C8H9NO2 详情 详情
(II) 21230 ethyl 2-(4-aminophenyl)acetate 5438-70-0 C10H13NO2 详情 详情
(III) 21231 ethyl 2-[4-(acetamido)phenyl]acetate C12H15NO3 详情 详情
Extended Information