Hydrochloric Acid → 2-(4-Fluorophenyl)-quinolin-3-ol

HRID 228847

Reaction equation

HRID 228847 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=O.[OH-:21].[Na+].Cl>CO.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:11]([OH:21])=[CH:4][C:3]3[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682552-AminobenzaldehydeHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 190675902-(4-Fluorophenyl)-quinolin-3-olYield 22.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Aminobenzaldehyde (118 mg) and 2-bromo-1-(4-fluoro-phenyl)-ethanone (225 mg) were dissolved in methanol (5 ml) to prepare a solution. Sodium hydroxide (100 mg) and water (5 ml) were added to the solution, and the mixture was stirred at room temperature overnight. 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 thin layer chromatography using ethyl acetate-hexane to give 2-(4-fluorophenyl)-quinolin-3-ol (53 mg, yield 22%).

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 thin layer chromatography

Sources & evidence

ORD record
ord-717d9670c44846bca936ad9d6a39e3e4
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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