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

HRID 1010209Notes

Reaction equation

HRID 1010209 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-def3c0198b5640eb9d308e72955bbe89
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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