Potassium Carbonate → Ethyl 1-cyclopropyl-6,8-difluoro-7-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 34575Notes

Reaction equation

HRID 34575 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:26]([F:27])=[C:25]([CH3:28])[C:24]([F:29])=[CH:23][C:9]=1[C:10]([C:12](=[CH:18][NH:19][CH:20]1[CH2:22][CH2:21]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11]>CN(C)C=O>[CH:20]1([N:19]2[C:23]3[C:9](=[CH:8][C:26]([F:27])=[C:25]([CH3:28])[C:24]=3[F:29])[C:10](=[O:11])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18]2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178471867HCID 178471867, compound

Product 1

HCID 13657408Ethyl 1-cyclopropyl-6,8-difluoro-7-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.5 g of potassium carbonate are added to a solution of 37.7 g of ethyl 2-(2-chloro-3,5-difluoro-4-methylbenzoyl)-3-cyclopropylamino-acrylate in 100 ml of anhydrous dimethylformamide. The reaction mixture is then stirred under reflux for 2 hours and poured hot onto ice. The precipitate is filtered off with suction, washed thoroughly with water and dried in vacuo over calcium chloride at 100° C. 30.4 g of ethyl 1-cyclopropyl-6,8-difluoro-7-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate of melting point 177°-179° C. are obtained.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionpoured hot onto ice
  3. filtrationThe precipitate is filtered off with suction
  4. washwashed thoroughly with water
  5. dry with materialdried in vacuo over calcium chloride at 100° C

Sources & evidence

ORD record
ord-256a0fee2ca5438e9be1846ee279c877
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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