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1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525888
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인쇄 미리보기

반응식

HRID 525888 반응식
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:28]=1[NH:37][CH:38]=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CCCCCC>[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:28]=1[NH:37][CH:38]=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41].[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]2[C:28]=1[NH:37][CH:38]=[C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:45]2=[O:47]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 86732752Diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate

생성물 2

HCID 86732752Diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonateHCID 86732753Ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 61%

시약·촉매·용매 1

HCID 8058
Hexane
용매

실험 절차

To Dowtherm (25 mL) heated at 250° C. was added diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate (10 g, 29.3 mmol). The mixture was stirred at the same temperature for 40 mins. LCMS indicated completion of the reaction. The reaction was allowed to cool at rt for 5 mins and was then poured into cold hexane, the yellow precipitate was collected by filtration, washed with hexane and dried in the air. This reaction was carried out in similar scale for several times. From a total of 72 g of diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate (211 mmol), ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (38 g, 129 mmol, 61.0% yield) was obtained as a yellow solid. LCMS (M+H)+: 296.0

후처리

  1. customcompletion of the reaction
  2. filtrationthe yellow precipitate was collected by filtration
  3. washwashed with hexane
  4. customdried in the air

출처 및 근거

ORD 기록
ord-9c8c52ae11254b36a17e745f6d08e698
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340556B2

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