Acetic Acid → 1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 248475Notes

Reaction equation

HRID 248475 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][C:12]([F:17])=[C:11]([F:18])[CH:10]=2)=[O:5])C.[OH-].[Na+].[C:21](O)(=O)[CH3:22]>Cl>[CH2:21]([N:8]1[C:9]2[C:14](=[CH:13][C:12]([F:17])=[C:11]([F:18])[CH:10]=2)[C:15](=[O:16])[C:6]([C:4]([OH:3])=[O:5])=[CH:7]1)[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178469610HCID 178469610, compound

Product 1

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A 4.1 g portion of the above ester in 50 ml of 37% hydrochloric acid was refluxed overnight, then cooled, basified with sodium hydroxide and then acidified with glacial acetic acid. The solid was collected, washed with water, methanol, ether and dried, giving 3.6 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. temperaturecooled
  2. customThe solid was collected
  3. washwashed with water, methanol, ether
  4. customdried

Sources & evidence

ORD record
ord-5778dd6985384f9696d4ea7a29a018f5
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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