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【结 构 式】

【分子编号】24553

【品名】methyl 6-acetyl-1-ethyl-7-hydroxy-4-oxo-8-propyl-1,4-dihydro-2-quinolinecarboxylate

【CA登记号】69049-70-3

【 分 子 式 】C18H21NO5

【 分 子 量 】331.36848

【元素组成】C 65.24% H 6.39% N 4.23% O 24.14%

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)

The alkylation of 4-(N-acetyl-N-ethylamino)-2-hydroxyacetophenone (I) with allyl bromide (II) by means of K2CO3 in DMF gives the allyl ether (III), which is isomerized by refluxing in diethylaniline to 4-(N-acetyl-N-ethylamino)-3-allyl-2-hydroxyacetophenone (IV) The reduction of (IV) with H2 over Pd/C in ethanol affords the corresponding propyl derivative (V), which is deacetylated with HBr in refluxing acetic acid water to 4-(ethylamino)-3-propyl-2-hydroxyacetophenone (VI). The addition of (VI) dimethyl acetylenedicarboxylate (VII) in refluxing ethanol affords the aminomaleate (VIII), which by cyclization witn polyphosphoric acid at 100 C gives methyl 1-ethyl-6-acetyl-7-hydroxy-4 oxo-8-propyl-4H-quinoline-2-carboxylate (IX). The condensation of (IX) with diethyl oxalate in DMF by means of NaH results in the ester of the final product (X), which is then hydrolyzed with NaHCO3 iin refluxing ethanol.

1 Wilkinson, D.J.; Lockley, W.J.S.; Synthesis of nedocromil sodium labelled with tritium, deuterium and carbon-14. J Label Compd Radiopharm 1985, 22, 9, 883.
2 Caims, H.; Cox, D. (Rhone-Poulenc Rorer Ltd.); Nouvelles pyranoquinoleinones et leurs compositions pharmaceutiques. DE 2819215; ES 469391; JP 1199909; JP 53137969 .
3 Cairns, H.; Cox, D. (Rhone-Poulenc Rorer Ltd.); 4,6-Dioxo-4H,6H-pyrano[3,2-g]quinoline-2,8-dicarbocyclic acids. GB 2022078 .
4 Prous, J.; Castaner, J.; Nedocromil sodium. Drugs Fut 1986, 11, 9, 756.
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) 17571 Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate 95-92-1 C6H10O4 详情 详情
(I) 24545 N-(4-acetyl-3-hydroxyphenyl)-N-ethylacetamide C12H15NO3 详情 详情
(II) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(III) 24547 3-[4-acetyl-3-(allyloxy)phenyl]-2-pentanone C16H20O3 详情 详情
(IV) 24548 N-(4-acetyl-2-allyl-3-hydroxyphenyl)-N-ethylacetamide 69049-64-5 C15H19NO3 详情 详情
(V) 24549 N-(4-acetyl-3-hydroxy-2-propylphenyl)-N-ethylacetamide C15H21NO3 详情 详情
(VI) 24550 1-[4-(ethylamino)-2-hydroxy-3-propylphenyl]-1-ethanone 69049-68-9 C13H19NO2 详情 详情
(VII) 24551 Dimethyl acetylenedicarboxylate; Dimethyl 2-butynedioate;Acetylenedicarboxylic acid dimethyl ester 762-42-5 C6H6O4 详情 详情
(VIII) 24552 dimethyl (Z)-2-[4-acetyl(ethyl)-3-hydroxy-2-propylanilino]-2-butenedioate 77941-04-9 C19H25NO6 详情 详情
(IX) 24553 methyl 6-acetyl-1-ethyl-7-hydroxy-4-oxo-8-propyl-1,4-dihydro-2-quinolinecarboxylate 69049-70-3 C18H21NO5 详情 详情
(X) 24554 diethyl 9-ethyl-4,6-dioxo-10-propyl-6,9-dihydro-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate 69049-72-5 C23H25NO7 详情 详情
Extended Information