4-Aminophenol → 4-(3-(Pyridin-4-yl)pyridin-2-yloxy)benzenamine

HRID 410190Notes

Reaction equation

HRID 410190 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[N:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:2]=1[O:21][C:18]1[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 463153642-Chloro-3-(pyridin-4-yl)pyridine

Product 1

HCID 593271694-(3-(Pyridin-4-yl)pyridin-2-yloxy)benzenamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a 50 mL round-bottomed flask was added 2-chloro-3-(pyridin-4-yl)pyridine (0.75031 g, 3.9 mmol), 4-aminophenol (0.4302 g, 3.9 mmol), cesium carbonate (0.38 ml, 4.7 mmol) in DMSO at 80° C. Upon completion, the reaction was allowed to cool to room temperature. The reaction mixture was diluted with water (10 ml) and extracted with DCM (3 15 mL). The organic extract was washed with water (1 10 mL), brine (1 10 mL), dried with magnesium sulfate, filtered and concentrated. The residue was taken up in DCM and was loaded onto a SCX cartridge. The impurities were filtered off with DCM and MeOH. 4-(3,4′-Bipyridin-2-yloxy)aniline was filtered from cartridge using 2.0M ammonia in MeOH (MS 264.0).

Workup

  1. extractionextracted with DCM (3 15 mL)
  2. extractionThe organic extract
  3. washwas washed with water (1 10 mL), brine (1 10 mL)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe impurities were filtered off with DCM and MeOH
  8. filtration4-(3,4′-Bipyridin-2-yloxy)aniline was filtered from cartridge

Sources & evidence

ORD record
ord-f933472267bf4fde9cb3c9e420121c25
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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