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

HRID 1915085Notes

Reaction equation

HRID 1915085 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-a11e142eb6a7407bbbe55cd7b2f0ae1f
Source dataset
uspto-grants-2013_12
Patent number
US08614234B2

Reaction notes

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