4-Aminophenol → 4-(4-Aminophenoxy)-6-chloropyridin-2-amine

HRID 521805Notes

Reaction equation

HRID 521805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1COCC1.Cl[C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17]([NH2:22])[CH:16]=1.O>CS(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:15]2[CH:20]=[C:19]([Cl:21])[N:18]=[C:17]([NH2:22])[CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 962WaterHCID 8028TetrahydrofuranHCID 53166492-Amino-4,6-dichloropyridine

Product 1

HCID 581678064-(4-Aminophenoxy)-6-chloropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 4-aminophenol (335 mg, 3.1 mmol) in anhydrous DMSO (8 ml) was flushed with nitrogen and treated with 1M KOBut/THF solution (3.1 ml, 3.1 mmol). The mixture was stirred at room temperature under nitrogen for 10 minutes. 4,6-dichloropyridin-2-ylamine (500 mg, 3.1 mmol) was added and the mixture was heated at 88° C. for 16 hours, cooled to room temperature and poured into 100 ml of water. The resulting precipitates were filtered, washed with water and dried to give the crude product, which was purified by silica gel chromatography with 2˜5% MeOH/CHCl3 to give 4-(4-aminophenoxy)-6-chloropyridin-2-amine as light brown solid. Yield: 350 mg, 49%.

Workup

  1. temperaturethe mixture was heated at 88° C. for 16 hours
  2. temperaturecooled to room temperature
  3. customThe resulting precipitates
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried
  7. customto give the crude product, which
  8. customwas purified by silica gel chromatography with 2˜5% MeOH/CHCl3

Sources & evidence

ORD record
ord-5b01820ef9cf4c3db15ae197be043e7f
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

Loading…