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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
Notes
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Reaction equation

HRID 525888 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 8058
Hexane
Solvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-9c8c52ae11254b36a17e745f6d08e698
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340556B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes