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【结 构 式】

【分子编号】35955

【品名】ethyl 4-chloro-3-quinolinecarboxylate

【CA登记号】

【 分 子 式 】C12H10ClNO2

【 分 子 量 】235.66964

【元素组成】C 61.16% H 4.28% Cl 15.04% N 5.94% O 13.58%

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:(V)

The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III), which is cyclized to ethyl 4-hydroxyquinoline-3-carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl. The reaction of (IV) with hot POCl3 affords ethyl 4-chloro-quinoline-3-carboxylate (V), which is finally cyclized with phenylhydrazine (VI) by heating at 105 C in xylene. (VI) is prepared in the usual way starting from aniline (I) by diazotation with NaNO2-HCl to phenyldiazonium chloride (VII), and reduction with SnCl2-HCl.

1 Yokoyama, N.; EP 0022078 .
2 Yokoyama, N.; US 4312870 .
3 Ritter, B.; Yokoyama, N.; Neubert, A.D.; 2-Arylpyrazolo[4,3-c]quinolin-3-ones: A partial novel agonist and antagonist of benzodiazepines. J Med Chem 1982, 25, 4, 337-339.
4 Serradell, M.N.; Grau, M.; Castaner, J.; Blancafort, P.; CGS-8216 and CGS-9896. Drugs Fut 1983, 8, 2, 99.
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) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(II) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(III) 35953 diethyl 2-(anilinomethylene)malonate C14H17NO4 详情 详情
(IV) 35954 ethyl 4-hydroxy-3-quinolinecarboxylate C12H11NO3 详情 详情
(V) 35955 ethyl 4-chloro-3-quinolinecarboxylate C12H10ClNO2 详情 详情
(VI) 11818 Phenyl hydrazine; 1-Phenylhydrazine 100-63-0 C6H8N2 详情 详情
(VII) 25897 benzenediazonium chloride C6H5ClN2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The condensation of aniline (I) with diethyl ethoxymethylenemalonate (II) by heating at 90 C gives diethyl anilinomethylenemalonate (III), which is cyclized to ethyl 4-hydroxyquinoline-3carboxylate (IV) by heating at 240 C in diphenyl ether-biphenyl. The reaction of (IV) with hot POCl3 affords ethyl-4-chloroquinoline-3-carboxylate (V), which is finally cyclized with 4-chlorophenylhydrazine (VIII) by heating at 105 C in xylene. (VIII) is prepared in the usual way starting from 4-chloroaniline (IX) by diazotation with NaNO2-HCl to 4-chlorophenyldiazonium chloride (X), and reduction with SnCl2-HCl.

1 Yokoyama, N.; US 4312870 .
2 Yokoyama, N.; EP 0022078 .
3 Ritter, B.; Yokoyama, N.; Neubert, A.D.; 2-Arylpyrazolo[4,3-c]quinolin-3-ones: A partial novel agonist and antagonist of benzodiazepines. J Med Chem 1982, 25, 4, 337-339.
4 Castaner, J.; Blancafort, P.; Grau, M.; Serradell, M.N.; CGS-8216 and CGS-9896. Drugs Fut 1983, 8, 2, 99.
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) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(II) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(III) 35953 diethyl 2-(anilinomethylene)malonate C14H17NO4 详情 详情
(IV) 35954 ethyl 4-hydroxy-3-quinolinecarboxylate C12H11NO3 详情 详情
(V) 35955 ethyl 4-chloro-3-quinolinecarboxylate C12H10ClNO2 详情 详情
(VIII) 33345 1-(4-chlorophenyl)hydrazine; 4-Chlorophenylhydrazine 1073-70-7 C6H7ClN2 详情 详情
(IX) 12034 4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline 106-47-8 C6H6ClN 详情 详情
(X) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
Extended Information