Water → 2-Phenyl-4-quinolone-6-carboxylic acid

HRID 986237Notes

Reaction equation

HRID 986237 reaction equation
[C:1]1([C:7]2[CH2:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:18]([O:20]C)=[O:19])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O>CO>[C:1]1([C:7]2[CH2:16][C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70432662Methyl 2-phenyl-4-quinolone-6-carboxylate

Product 1

HCID 704325112-Phenyl-4-quinolone-6-carboxylic acidYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-phenyl-4-quinolone-6-carboxylate (3.8 grams) obtained in Example 1 is refluxed for three hours in a mixture of 100 ml of methanol, 3 grams of sodium hydroxide and 15 ml of water. The mixture is evaporated to dryness in vacuo, 100 ml of water is added to the residue, filtered, acidified with 10% hydrochloric acid solution, and the crystals which separate out therefrom are collected by filtration. These are recrystallized from dimethyl formamide to give 2.8 grams of 2-phenyl-4-quinolone-6-carboxylic acid, colorless powder, melting at above 300° C.

Workup

  1. customThe mixture is evaporated to dryness in vacuo, 100 ml of water
  2. additionis added to the residue
  3. filtrationfiltered
  4. customthe crystals which separate out
  5. filtrationtherefrom are collected by filtration
  6. customThese are recrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-9801e1a0b6d2406bb9784b4a54fa9a1d
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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