丙二酸二乙酯 → Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate

HRID 3147

反应方程式

HRID 3147 反应方程式
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:13](OCC)(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH:1]([N:4]1[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]1=[O:20])([CH3:3])[CH3:2]

参与物

5

反应物 3

HCID 7761丙二酸二乙酯HCID 516892碳酸氢钠HCID 110410352-((Propan-2-yl)amino)benzaldehyde

产物 1

HCID 15468682Ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate收率 61.3%

试剂、催化剂与溶剂 1

HCID 7918乙酐溶剂

反应条件

温度
100 °C

实验过程

A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 7.3 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate.

后处理

  1. customAfter evaporation of the solvent under reduced pressure, water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting oily substance was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

来源与证据

ORD记录
ord-6ea71cac5fe24314936a22d13c05f389
来源数据集
uspto-grants-1998_03
专利号
US05733917

关联笔记

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