磷酸三乙酯 → Ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525949笔记

反应方程式

HRID 525949 反应方程式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][NH:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].P(OCC)(OCC)(O[CH2:30][CH3:31])=O>O>[CH2:30]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=2[O:13][CH3:14])[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]1)[CH3:31]

参与物

5

反应物 3

HCID 6535磷酸三乙酯HCID 11430碳酸钾HCID 86732817Ethyl 4-hydroxy-7,8-dimethoxyquinoline-3-carboxylate

产物 1

HCID 15675313Ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate收率 59%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
120 °C

实验过程

A mixture of ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (40 g, 144 mmol) and potassium carbonate (29.9 g, 216 mmol) in triethyl phosphate (123 ml, 721 mmol) was stirred at 120° C. for 24 h. LCMS indicated completion of the reaction. The reaction mixture was cooled down to rt and diluted with water, extracted with DCM, dried over sodium sulfate and evaporated in vacuo. The crude material was recrystallized in EtOH, the precipitate was collected by filtration, washed by cold EtOH and dried in air to afford ethyl 1-ethyl-7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (26 g, 85 mmol, 59.0% yield) as a yellow solid. LCMS: (M+H)+: 306.2.

后处理

  1. customcompletion of the reaction
  2. temperatureThe reaction mixture was cooled down to rt
  3. extractionextracted with DCM
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude material was recrystallized in EtOH
  7. filtrationthe precipitate was collected by filtration
  8. washwashed by cold EtOH
  9. customdried in air

来源与证据

ORD记录
ord-7090ebedfdb8456c86d6328edb9893ff
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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