Hydrochloric Acid → 2-(2,4-Difluoro-phenyl)-quinolin-3-ol

HRID 228849

Reaction equation

HRID 228849 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])=O.[OH-:22].[Na+].Cl>CO.O>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[C:12]1[C:11]([OH:22])=[CH:4][C:3]2[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682552-AminobenzaldehydeHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 230785092-(2,4-Difluoro-phenyl)-quinolin-3-olYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Aminobenzaldehyde (360 mg) and 2-chloro-1-(2,4-difluoro-phenyl)-ethanone (585 mg) were dissolved in methanol (15 ml) to prepare a solution. Sodium hydroxide (310 mg) and water (3 ml) were added to the solution, and the mixture was stirred at room temperature overnight. A dilute hydrochloric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using ethyl acetate-hexane to give 2-(2,4-difluoro-phenyl)-quinolin-3-ol (237 mg, yield 41%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-dcdb4fd8ae3a4aeebc5a32bb4d3cf2a3
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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