Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate → 6,7-Difluoro-1,4-dihydro-1-methyl-4-oxo-3-quinolinecarboxylic acid

HRID 2247922Notes

Reaction equation

HRID 2247922 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]([CH3:19])[CH:7]=1)=[O:5])C>Cl>[F:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[F:18])[N:8]([CH3:19])[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16]

Participants

3

Reactant 1

HCID 14423855Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 107763686,7-Difluoro-1,4-dihydro-1-methyl-4-oxo-3-quinolinecarboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6,7-Difluoro-1,4-dihydro-1-methyl-4-oxo-quinoline-3-carboxylic acid ethyl ester (7.24 g, 27.1 mmol) was mixed with 1N hydrochloric acid (300 ml) and heated to reflux for 2 hours. The reaction mixture was filtered, and the precipitate washed with water and dried under vacuum to provide the title product as a white solid, m.p. 284°-287° (5.78 g, 24.2 mmol, 89% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4fd64525bb0d430eaf25a0888b4cb924
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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