Isatin → 2-(3,4-Difluorophenyl)-4-quinolinecarboxylic acid

HRID 411514Notes

Reaction equation

HRID 411514 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[C:2]1=[O:11].[F:12][C:13]1[CH:14]=[C:15]([C:20](=O)[CH3:21])[CH:16]=[CH:17][C:18]=1[F:19].[OH-:23].[K+]>O1CCOCC1>[F:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:3]([C:2]([OH:11])=[O:23])[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

5

Reactant 3

HCID 7054IsatinHCID 14797Potassium HydroxideHCID 1230521-(3,4-Difluorophenyl)ethan-1-one

Product 1

HCID 46116332-(3,4-Difluorophenyl)-4-quinolinecarboxylic acidYield 5.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2,3-indolinedione (5 g, 0.03 mole), 3′,4′-difluoroacetophenone (5 g, 0.03 mole) and potassium hydroxide (3 g, 0.05 mole) in 1,4-dioxane (50 mL) is heated at 105° C. for 48 hours. The reaction solution is then cooled to room temperature and concentrated under reduced pressure. The residue is treated with EtOAc and extracted with water. The pH of the aqueous layer is adjusted to 5-6 with 1N HCl, the resulting solid is collected by vacuum filtration, washed with water, and dried to give the titled compound (450 mg) as a yellow solid.

Workup

  1. temperatureThe reaction solution is then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is treated with EtOAc
  4. extractionextracted with water
  5. filtrationthe resulting solid is collected by vacuum filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-ba1a3861c38f4b82a8002ce411707de2
Source dataset
uspto-grants-2003_05
Patent number
US06559163B2

Reaction notes

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