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Water → Ethyl 7-bromo-1-cyclopropyl-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1461384
Notes
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Reaction equation

HRID 1461384 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:26]([F:27])=[C:25](F)[C:11]([C:12]([C:14](=[CH:20][NH:21][CH:22]2[CH2:24][CH2:23]2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[C:10]([F:29])[C:9]=1[F:30].O>CN(C)C=O>[Br:7][C:8]1[C:26]([F:27])=[C:25]2[C:11]([C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][N:21]2[CH:22]2[CH2:24][CH2:23]2)=[C:10]([F:29])[C:9]=1[F:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178471890HCID 178471890, compound

Product 1

HCID 11741084Ethyl 7-bromo-1-cyclopropyl-5,6,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Potassium carbonate (30 g) was added to a stirred solution/suspension of 31.65 g ethyl 2-(4-bromo-2,3,5,6-tetrafluorobenzoyl)-3-cyclopropylaminopropenoate in 300 ml dimethylformamide. The mixture was heated at 150° C. for 1.5 hours, then cooled, poured into water and extracted with methylene dichloride. The extract was washed with water and sodium chloride solution, dried (magnesium sulfate) and concentrated. The residue was recrystallized from acetonitrile to give 19.3 g (64%) ethyl 7-bromo-1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, m.p. 187°-189° C.

Workup

  1. temperaturecooled
  2. extractionextracted with methylene dichloride
  3. washThe extract was washed with water and sodium chloride solution
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b4161097d0fd41f6a9244f3c2a4717bf
Source dataset
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05075319

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes