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Malonate Ion → Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525934
Notes
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Reaction equation

HRID 525934 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9084Malonate IonHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 86732800Diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonateHCID 86732802Ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3d1f5c85dcb44d7a8c071f54d74ad8e
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340556B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes