Water → 3-Benzoyl-2,4-dihydroxyquinoline-5-carboxylic acid

HRID 370467Notes

Reaction equation

HRID 370467 reaction equation
[C:1]([C:9]1[C:10](=[O:24])[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:20]([O:22]C)=[O:21])[C:17]=2[C:18]=1[OH:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O>CS(C)=O>[C:1]([C:9]1[C:10](=[O:24])[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:20]([OH:22])=[O:21])[C:17]=2[C:18]=1[OH:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 135687072Methyl 3-benzoyl-2,4-dihydroxyquinoline-5-carboxylate

Product 1

HCID 1356870743-Benzoyl-2,4-dihydroxyquinoline-5-carboxylic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 0.6 grams of methyl 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylate are added 1.5 grams of sodium hydroxide, 30 ml of water and 30 ml of dimethyl sulfoxide, the mixture is heated at 100° to 120° C. for three hours with stirring, cooled, acidified and diluted hydrochloric acid, and crystals separated out therefrom are collected by filtration to give 0.54 grams of 3-benzoyl-4-hydroxy-2-quinolone-5-carboxylic acid, colorless powder, melting at above 300° C.

Workup

  1. temperaturethe mixture is heated at 100° to 120° C. for three hours
  2. temperaturecooled
  3. customdiluted hydrochloric acid, and crystals separated
  4. filtrationout therefrom are collected by filtration

Sources & evidence

ORD record
ord-1f4b15e408124c9db6a41139dcb53b3a
Source dataset
uspto-grants-1985_07
Patent number
US04526894

Reaction notes

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