4-Aminophenol → 2-Amino-4-(4-aminophenoxy)pyridine

HRID 520697Notes

Reaction equation

HRID 520697 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=1.O(C)[Na]>CS(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 5818662-Amino-4-chloropyridineHCID 178418582HCID 178418582, compound

Product 1

HCID 229367412-Amino-4-(4-aminophenoxy)pyridineYield 26%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 4-aminophenol (218 mg, 2 mmol) and 4-chloropyridin-2-amine (256 mg, 2 mmol) in DMSO (2.5 mL) was added NaOCH3 (216 mg, 4 mmol). The reaction was microwaved at 180° C. for 40 minutes, then cooled down to rt and quenched with water (10 mL). The mixture was extracted with EtOAc (10 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=30/1) to give the title compound as a brown solid (103 mg, 26%).

Workup

  1. customThe reaction was microwaved at 180° C. for 40 minutes
  2. customquenched with water (10 mL)
  3. extractionThe mixture was extracted with EtOAc (10 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (DCM/CH3OH (v/v)=30/1)

Sources & evidence

ORD record
ord-9a038902117e4c6d9a1378d221060bff
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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