Sodium Hydroxide → 1-(1,1-Dimethylethyl)-1,4-dihydro-6,7-difluoro-4-oxo-3-quinolinecarboxylic acid

HRID 1089223Notes

Reaction equation

HRID 1089223 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([F:18])=[C:12]([F:17])[CH:13]=2)[N:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[F:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[F:18])[N:8]([C:19]([CH3:21])([CH3:22])[CH3:20])[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14612522HCID 14612522, compound

Product 1

HCID 148395931-(1,1-Dimethylethyl)-1,4-dihydro-6,7-difluoro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.08 g (19.7 mmoles) of 6,7-difluoro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester and 19.7 mmoles of 2N aqueous sodium hydroxide in 80 mL of ethanol was stirred overnight. The resulting mixture was concentrated in vacuo, taken up with 200 mL of water and extracted with dichloromethane. About 8 mL of 2N HCl was added to the aqueous layer to adjust the pH to 3. The precipitate was collected by filtration, washed with H2O and dried to give 4.47 g, of titled compound. MP >260° C.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane
  3. additionAbout 8 mL of 2N HCl was added to the aqueous layer
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with H2O
  6. customdried
  7. customto give 4.47 g

Sources & evidence

ORD record
ord-db219fd19ba64714b473a95e754fff39
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

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