Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate → HCID 178524724, compound

HRID 48284Notes

Reaction equation

HRID 48284 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([O:14]CC)=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1>[OH-].[Na+]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178469609Ethyl 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 178524724HCID 178524724, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of ethyl 7-fluoro-4-hydroxy-3-quinolinecarboxylate (65 g, 0.28 mol) in 10% sodium hydroxide (250 mL) was heated at reflux for 3 hours during which time a solution was obtained. The reaction mixture was allowed to cool to ambient temperature and then it was filtered through filter paper under vacuum. The filtrate was acidified with concentrated hydrochloric acid. The resulting precipitate was collected, washed with water and then dried to provide 53.5 g of 7-fluoro-4-hydroxy-3-quinolinecarboxylic acid as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours during which time a solution
  3. customwas obtained
  4. filtrationit was filtered
  5. filtrationthrough filter paper under vacuum
  6. customThe resulting precipitate was collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f28ef299875b4284b0cccbc9415ff5f2
Source dataset
uspto-grants-2004_03
Patent number
US06703402B2

Reaction notes

Loading…