Potassium Carbonate → Ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 47892Notes

Reaction equation

HRID 47892 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([C:9]1[C:10](Cl)=[C:11]([CH:25]=[C:26]([F:29])[C:27]=1[Cl:28])[C:12]([C:14](=[CH:20][NH:21][CH:22]1[CH2:24][CH2:23]1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])#[N:8]>CN(C=O)C>[C:7]([C:9]1[C:27]([Cl:28])=[C:26]([F:29])[CH:25]=[C:11]2[C:10]=1[N:21]([CH:22]1[CH2:24][CH2:23]1)[CH:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:12]2=[O:13])#[N:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178471869HCID 178471869, compound

Product 1

HCID 23431783Ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
42.5 °C

Procedure

34.7 g of anhydrous K2CO3 (0.35 mol) was added to a solution of 64.2 g of ethyl 2-(3-cyano-2,4-dichloro-5-fluorobenzoyl)-3-cyclopropylaminoacrylate (0.173 mol) in 220 ml of DMF. The reacting mixture was stirred at 40-45° C. for 2.5 hours, and the reaction was monitored by TLC. The reactant was then poured into 800 ml of ice-water, filtered, washed with water (100 ml×2), and dried. The resultant solid was dissolved in 120 ml of 95% ethanol and then refluxed for 15 minutes, cooled, filtered and dried to afford 53.2 g of ethyl 8-cyano-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.159 mol) as a white solid, mp 196-199° C., in 90.1% yield.

Workup

  1. filtrationfiltered
  2. washwashed with water (100 ml×2)
  3. customdried
  4. dissolutionThe resultant solid was dissolved in 120 ml of 95% ethanol
  5. temperaturerefluxed for 15 minutes
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-69728d7d94ab41a1b3022298879b6eb1
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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