【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% |
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 |