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【结 构 式】

【分子编号】47908

【品名】2-(2-amino-5-chlorophenyl)acetic acid

【CA登记号】

【 分 子 式 】C8H8ClNO2

【 分 子 量 】185.60976

【元素组成】C 51.77% H 4.34% Cl 19.1% N 7.55% O 17.24%

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:(IX)

5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide (X), a key intermediate in the synthesis of tenidap, has been obtained by several different ways, all of them starting from 5-chloro-2,3-dihydro-1H-indol-2-one (I). 1. The reaction of indolone (I) with cyclohexylcarbonyl isocyanate (II) gives the N-acyl carboxamide (III), which is treated with KOH to yield 2-(5-chloro-2-ureidophenyl)acetic acid (IV). Finally, this compound is cyclized to the target carboxamide by treatment with trifluoroacetic anhydride and trifluoroacetic acid. 2. The reaction of indolone (I) with isobutyryl isocyanate (XI) gives the N-acyl carboxamide (V), which is treated with KOH to yield 2-(5-chloro-2-ureidophenyl)acetic acid (III). Finally, this compound is cyclized to the target carboxamide as before. 3. The reaction of indolone (I) with trichloroacetyl isocyanate (VI) in hot toluene gives the target carboxamide in one step. 4. The reaction of indolone (I) with chlorosulfonyl isocyanate (VII) gives the N-chlorosulfonyl carboxamide (VIII), which is hydrolyzed to the target carboxamide with aqueous acetic acid. 5. The reaction of indolone (I) with NaOH and then with H2SO4 gives 2-(2-amino-5-chlorophenyl)acetic acid (IX), which is treated with potassium isocyanate and AcOH to yield 2-(5-chloro-2-ureidophenyl)acetic acid (III). Finally, this compound can be cyclized to the target intermediate by means of AcOH and NaOAc.

1 Sarma, M.R.; Goud, P.S.; Sailaja, M.; Kumar, P.R.; Reddy, G.O.; Raju, S.; Synthesis of tenidap: An improved process for the preparation of 5-chloro-2-oxindole-1-carboxamide. Org Process Res Dev 2001, 5, 1, 61.
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) 14100 5-Chlorooxindole; 5-Chloro-1,3-dihydro-2H-indol-2-one 17630-75-0 C8H6ClNO 详情 详情
(II) 47903 cyclohexanecarbonyl isocyanate C8H11NO2 详情 详情
(III) 47904 5-chloro-N-(cyclohexylcarbonyl)-2-oxo-1-indolinecarboxamide C16H17ClN2O3 详情 详情
(IV) 47905 2-[2-[(aminocarbonyl)amino]-5-chlorophenyl]acetic acid C9H9ClN2O3 详情 详情
(V) 47906 5-chloro-N-isobutyryl-2-oxo-1-indolinecarboxamide C13H13ClN2O3 详情 详情
(VI) 40725 2,2,2-trichloroacetyl isocyanate 3019-71-4 C3Cl3NO2 详情 详情
(VII) 14101 Chlorosulfonyl isocyanate 1189-71-5 CClNO3S 详情 详情
(VIII) 47907 5-chloro-1-[[(chlorosulfonyl)amino]carbonyl]-2-oxoindoline C9H6Cl2N2O4S 详情 详情
(IX) 47908 2-(2-amino-5-chlorophenyl)acetic acid C8H8ClNO2 详情 详情
(X) 14096 5-Chloro-2-oxo-1-indolinecarboxamide C9H7ClN2O2 详情 详情
(XI) 47909 2-methylpropanoyl isocyanate C5H7NO2 详情 详情
Extended Information