Ethyl 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate → 6-Methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 228864Notes

Reaction equation

HRID 228864 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][CH:8]=[C:7]([C:14]([O:16]CC)=[O:15])[C:6]2=[O:19]>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][CH:8]=[C:7]([C:14]([OH:16])=[O:15])[C:6]2=[O:19]

Participants

3

Reactant 1

HCID 12369042Ethyl 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate

Product 1

HCID 123690366-Methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate (25.5 g) was suspended in a 2 M aqueous sodium hydroxide solution (250 ml), and the mixture was heated under reflux for 4 hr. The reaction solution was cooled to room temperature, the aqueous layer was then washed with chloroform and was neutralized with dilute hydrochloric acid. The precipitated crystal was collected by filtration and was washed with water, isopropanol, and hexane in that order to give 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (22.1 g, yield 98%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. washthe aqueous layer was then washed with chloroform
  4. filtrationThe precipitated crystal was collected by filtration
  5. washwas washed with water, isopropanol, and hexane in that order

Sources & evidence

ORD record
ord-a435b2078c944f388bd4f04110d56ab9
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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