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【结 构 式】 
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【分子编号】23031 【品名】7,8-dimethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-2-carbonyl chloride 【CA登记号】 |
【 分 子 式 】C15H10ClNO4 【 分 子 量 】303.70144 【元素组成】C 59.32% H 3.32% Cl 11.67% N 4.61% O 21.07% |
合成路线1
该中间体在本合成路线中的序号：(VII)1) The cyclization of 2,3-dimethylaniline (I) with diethyl acetylmalonate (II) in 1-chloronaphthalene at 240 C gives 3-acetyl-4-hydroxy-7,8-dimethylquinolin-2(1H)-one (III), which by reaction with diethyl oxalate (IV) by means of sodium ethoxide in refluxing benzene yields ethyl-4-(4-hydroxy-7,8-dimethyl-2-oxo-1,2-dihydroquinolin-3yl)-2,4-dioxo-butanoate (V). The cyclization of (V) in acetic acid concentrated HCl at 100 C affords 5,6-dihydro-7,8 dimethyl-4,5-dioxo-4H-pyrano[3,2-c]quinoline-2-carboxylic acid (VI), which is converted into the corresponding acyl chloride (VII) by reaction with refluxing SOCl2. Finally, this compound is treated with hot 3-methylbutanol (VIII).
| 【1】 Takahashi, K.; Hata, S.; Morinaka, Y.; Yamada, S.; Antiallergic agents I. Pyranoquinoline derivatives. Eur J Med Chem - Chim Ther 1981, 16, 3, 251. |
| 【2】 Castaner, J.; Prous, J.; Repirinast. Drugs Fut 1987, 12, 1, 37. |
| 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) | 23025 | 2,3-Dimethylphenylamine; 2,3-Dimethylaniline; 2,3-Xylidine | 87-59-2 | C8H11N | 详情 | 详情 |
| (II) | 23026 | diethyl 2-acetylmalonate | 570-08-1 | C9H14O5 | 详情 | 详情 |
| (III) | 23027 | 3-acetyl-4-hydroxy-7,8-dimethyl-2(1H)-quinolinone | C13H13NO3 | 详情 | 详情 | |
| (IV) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (V) | 23029 | ethyl 4-(4-hydroxy-7,8-dimethyl-2-oxo-1,2-dihydro-3-quinolinyl)-2,4-dioxobutanoate | C17H17NO6 | 详情 | 详情 | |
| (VI) | 24014 | Phenyllithium | 591-51-5 | C6H5Li | 详情 | 详情 |
| (VII) | 23031 | 7,8-dimethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-2-carbonyl chloride | C15H10ClNO4 | 详情 | 详情 | |
| (VIII) | 23032 | 3-methyl-1-butanol | 123-51-3 | C5H12O | 详情 | 详情 |