Ethanol → HCID 12150700, compound

HRID 1837326Notes

Reaction equation

HRID 1837326 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14]CC)=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:18][CH3:19].[OH-].[Na+].C(O)C.O>C(O)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([OH:14])=[O:13])=[CH:8][NH:9]2)=[CH:4][C:3]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 12150699ETHYL 7-FLUORO-4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLATE

Product 1

HCID 12150700HCID 12150700, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 7-fluoro-6-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylate (2.2 g, 8.30 mmol) and 13.2 mL of 1 N sodium hydroxide and 40 mL of ethanol is heated at reflux for 3 hours then cooled to room temperature. Water is added and the mixture is acidified with acetic acid. The resultant solid is collected by filtration washing with water to provide 1.90 g of 7-fluoro-6-methoxy-4-oxo-1,4,-dihydro-3-quinolinecarboxylic acid as a white solid, mp 265-267° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe resultant solid is collected by filtration
  4. washwashing with water

Sources & evidence

ORD record
ord-978fbb97423d477ab96a2319da53ab11
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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