Potassium Carbonate → Methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 47889Notes

Reaction equation

HRID 47889 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[C:25]([O:26][CH3:27])=[C:24]([Cl:28])[C:23]([F:29])=[CH:22][C:9]=1[C:10]([C:12](=[CH:17][NH:18][CH:19]1[CH2:21][CH2:20]1)[C:13]([O:15][CH3:16])=[O:14])=[O:11]>CN(C=O)C>[CH:19]1([N:18]2[C:8]3[C:9](=[CH:22][C:23]([F:29])=[C:24]([Cl:28])[C:25]=3[O:26][CH3:27])[C:10](=[O:11])[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17]2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178500746HCID 178500746, compound

Product 1

HCID 23431770Methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 90.3%

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 62.6 g of methyl 2-(2,4-dichloro-5-fluoro-3-methoxybenzoyl)-3-cyclopropylaminoacrylate in 220 ml of DMF. The reactant was stirred at 40-45° C. for 2.5 hours, and the reaction was monitored by TLC. The resulting mixture was then poured into 800 ml of ice-water, filtered, washed with water (100 ml×2), and dried. The resulting solid was dissolved in 120 ml of 95% methanol and then refluxed for 15 minutes, cooled, filtered and dried to afford 50.8 g of methyl 1-cyclopropyl-7-chloro-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.156 mol) as a white solid, mp 184-187C., in 90.1% yield.

Workup

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

Sources & evidence

ORD record
ord-cdc1ad45c8bc4a67a41b0b5918881b50
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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