5-Methylisatin → HCID 15376151, compound

HRID 1956759Notes

Reaction equation

HRID 1956759 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].[C:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21])(=O)[CH3:16]>O>[C:20]([C:19]1[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=1[C:15]1[CH:16]=[C:5]([C:6]([OH:11])=[O:13])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[N:7]=1)([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 118405-MethylisatinHCID 14798Sodium HydroxideHCID 684742-Acetylbenzoic acid

Product 1

HCID 15376151HCID 15376151, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To 9.93 ml of water were added 10.0 g (62.1 mmol) of 5-methylisatin obtained in Example 1 and 4.96 g (0.12 mol) of sodium hydroxide. 10.2 g (62.1 mmol) of 2-acetylbenzoic acid was added thereto and the mixture was heated to 90° C. under reflux. The mixture was heated further at 115° C. for one hour after the reaction became mild. Thereafter, the mixture was allowed to cool to room temperature and poured into 200 g of iced water. The aqueous layer was washed with ether and acidified with 2M hydrochloric acid. The formed precipitate was collected by filtration to obtain 6.55 g of 2-(2-carboxyphenyl)-6-methyl-4-quinolinecarboxylic acid. NMR (270 MHz, Acetone-d6):

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was heated further at 115° C. for one hour after the reaction
  3. temperatureto cool to room temperature
  4. washThe aqueous layer was washed with ether
  5. filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-9491e3200ba84bad9fe7ef6c82d76204
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

Loading…