Isatin → 2-(2-Carboxyphenyl)-4-quinolinecarboxylic acid

HRID 1956765Notes

Reaction equation

HRID 1956765 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-:12].[Na+].[C:14]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])(=O)[CH3:15]>O>[C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=1[C:14]1[CH:15]=[C:4]([C:2]([OH:12])=[O:3])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1)([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 7054IsatinHCID 14798Sodium HydroxideHCID 684742-Acetylbenzoic acid

Product 1

HCID 167673762-(2-Carboxyphenyl)-4-quinolinecarboxylic acidYield 33.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

In 15 ml of water were dissolved 14.7 g (0.1 mol) of isatin and 8 g (0.2 mol) of sodium hydroxide. Then, 16.4 g (0.1 mol of 2-acetylbenzoic acid was added thereto and the resulting mixture was heated at 90° C. under reflux. When the reaction became mild, the mixture was heated at 115° C. for an additional 1 hour. After allowing to cool to room temperature, it was poured into 300 g of water cooled with ice. The aqueous layer was washed with ether and acidified with 2M hydrochloric acid. The precipitate thus formed was collected by filtration to thereby give 9.85 g of 2-(2-carboxyphenyl)-4-quinolinecarboxylic acid. NMR (270 MHz, CD3COCD3): δ 7.70-8.70 (m,9H).

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was heated at 115° C. for an additional 1 hour
  3. temperatureto cool to room temperature
  4. temperaturecooled with ice
  5. washThe aqueous layer was washed with ether
  6. customThe precipitate thus formed
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8f7a1be3744644c08fc6aedc0da7de6a
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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