4-Aminophenol → 4-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}aniline

HRID 568997Notes

Reaction equation

HRID 568997 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=1>O.CS(C)=O>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:3])=[CH:5][CH:6]=2)=[N:13][CH:14]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 14797Potassium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 27830854-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}aniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

11.2 g (0.2 mole) of potassium hydroxide in 15 ml of water are added dropwise under nitrogen atmosphere to 22 g (0.2 mole) of 4-aminophenol in 100 ml of diemthylsulfoxide. 36 g (0.2 mole) of 2-chloro-5-(trifluoromethyl)pyridine in 30 ml of dimethylsulfoxide are added dropwise at 25° C. The reaction mixture is stirred for 3 hours at room temperature, then poured into ice-water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is dissolved in ether and the ether solution is extracted with 1 N hydrochloric acid. The acid phase is made alkaline with concentrated NaOH solution and extracted with ether. The ether phase is dried over sodium sulfate and concentrated by evaporation, affording 4-(5-trifluoromethylpyridin-2-yl-oxy)aniline as a brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated by evaporation
  4. dissolutionThe residue is dissolved in ether
  5. extractionthe ether solution is extracted with 1 N hydrochloric acid
  6. extractionextracted with ether
  7. dry with materialThe ether phase is dried over sodium sulfate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1eda24ee94df455c961c31cc8255e7ba
Source dataset
uspto-grants-1988_03
Patent number
US04731090

Reaction notes

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