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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
ノート
印刷プレビュー

反応式

HRID 525888 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8058
Hexane
溶媒

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-9c8c52ae11254b36a17e745f6d08e698
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340556B2

反応ノート

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