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丙二酸 → Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525934
笔记
打印预览

反应方程式

HRID 525934 反应方程式
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[F:26][C:27]1[CH:28]=[C:29]([NH:37][CH:38]=[C:39]([C:45]([O:47]CC)=O)[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34].C([O-])(=O)CC([O-])=O.FC1C(OC)=C(OC)C=C2C=1C(=O)C(C(OCC)=O)=CN2>CCCCCC>[F:26][C:27]1[CH:28]=[C:29]2[C:30]([C:45](=[O:47])[C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][NH:37]2)=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34]
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

6

反应物 4

HCID 9084丙二酸HCID 24670二苯醚-联苯共晶HCID 86732800Diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonateHCID 86732802Ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

产物 1

HCID 86732801Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate收率 80%

试剂、催化剂与溶剂 1

HCID 8058正己烷溶剂

反应条件

温度
250 °C

实验过程

To Dowtherm (150 mL) heated at 250° C. was added diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonate (30 g, 87 mmol). The mixture was stirred at 250° C. for 30 min. LCMS indicated completion of the reaction. The reaction mixture was allowed to cool a bit and was then added to cold hexane, the precipitates were collected by filtration, washed with hexane and then allowed to dry in the air. Similar scale reactions were repeated several times. From a total amount of the malonate (148 g, 434 mmol), a mixture of ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate and ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate was obtained as brown solid without further purification (103 g, 349 mmol, 80% yield). LCMS: (M+H)+: 296.1.

后处理

  1. customcompletion of the reaction
  2. temperatureto cool a bit
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with hexane
  5. customto dry in the air

来源与证据

ORD记录
ord-e3d1f5c85dcb44d7a8c071f54d74ad8e
来源数据集
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09340556B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记