Hydrochloric Acid → 4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID

HRID 2227157Notes

Reaction equation

HRID 2227157 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]([C:13]([O:15]CC)=[O:14])[C:6]2=[O:18].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]([C:13]([OH:15])=[O:14])[C:6]2=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 228284Ethyl 6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 2552894-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACIDYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylate (1.22 g, 4.96 mmol), 1N NaOH (25 mL), and ethanol (5 mL) is heated at reflux for 1.5 h. The reaction mixture is cooled in an ice bath, acidified with aqueous HCl, and the precipitate is collected, rinsed with water and dried to give 0.95 g of 6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 h
  3. temperatureThe reaction mixture is cooled in an ice bath
  4. customthe precipitate is collected
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-2060e8c68ca24dcea6390d3260aaf16e
Source dataset
uspto-grants-2002_07
Patent number
US06413956B1

Reaction notes

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