Dimethyl Sulfoxide → 4-(4-Amino-3-chlorophenoxy)pyridin-2-ylamine

HRID 1433474Notes

Reaction equation

HRID 1433474 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[Cl:17].[H-].[Na+].CS(C)=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([O:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[C:11]([Cl:17])[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 871844-Amino-3-chlorophenolHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 229367984-(4-Amino-3-chlorophenoxy)pyridin-2-ylamineYield 55.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The publicly known compound 2-amino-4-chloropyridine (5.0 g), 4-amino-3-chlorophenol (11 g), sodium hydride (60% in oil) (3.1 g) and dimethylsulfoxide (80 ml) were stirred at 160° C. for 9.5 hours. Water was added, extraction was performed with ethyl acetate, and the extract solution was washed 5 times with water. The extract solution was then passed through a glass filter coated with silica gel. The silica gel was washed with ethyl acetate, the ethyl acetate layers were combined, and the solvent was distilled off under reduced pressure to obtain 5.1 g of a dark violet solid.

Workup

  1. extractionextraction
  2. washthe extract solution was washed 5 times with water
  3. filtrationfilter
  4. washThe silica gel was washed with ethyl acetate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ba1957c9362d49749f08c0dca1b2c858
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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