4-Aminophenol → 4-(2-Chloro-pyridin-4-yloxy)-phenylamine

HRID 521783Notes

Reaction equation

HRID 521783 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1COCC1.[Cl:14][C:15]1[CH:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1.O>CS(C)=O>[Cl:14][C:15]1[CH:20]=[C:19]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 962WaterHCID 8028TetrahydrofuranHCID 335152,4-Dichloropyridine

Product 1

HCID 578334304-(2-Chloro-pyridin-4-yloxy)-phenylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 4-aminophenol (740 mg, 6.8 mmol) in anhydrous DMSO (8 ml) was flushed with nitrogen and treated with 1M KOBut/THF solution (10 ml, 10 mmol). The mixture was stirred at room temperature under nitrogen for 10 minutes. 2,4-dichloropyridine (1.0 g, 6.8 mmol) was added and the mixture was heated at 60° C. for 30 minutes, cooled to room temperature and poured into 100 ml of water. The resulting precipitates were filtered, washed with water and dried to give 4-((2-chloropyridin-4-yl)oxy)aniline as light brown solid. The material was used for the following reactions without further purification. Yield: 1.15 g, 77%.

Workup

  1. temperaturethe mixture was heated at 60° C. for 30 minutes
  2. temperaturecooled to room temperature
  3. customThe resulting precipitates
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-48282333cc434a798b850c36a52c363b
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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