Sodium Hydroxide → 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide

HRID 2066279Notes

Reaction equation

HRID 2066279 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.CC(C)([O-])C.[K+].Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:24]([NH2:26])=[O:25])[CH:19]=1.[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]([NH2:26])=[O:25])[CH:19]=2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 3035434-Chloropyridine-2-carboxamideHCID 27787624-Amino-2,5-difluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 247886284-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Amino-2,5-difluorophenol (4.95 g) was dissolved in dimethyl sulfoxide (50 ml) under a nitrogen flow, and potassium tert-butoxide (4.05 g) was added at room temperature, followed by stirring for 25 min. 4-Chloropyridine-2-carboxamide (2.70 g) was added thereto, followed by stirring at 80° C. for 2.5 hr. The reaction mixture was allowed to cool down to room temperature, and a 1N aqueous solution of sodium hydroxide (74.25 ml) was added, followed by stirring for 10 hr. The precipitated solid was collected by filtration, and the resultant solid was washed with water. This solid was dried under hot air at 100° C. for 24 hr to provide the titled compound as purple powder (3.38 g, 74%).

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at 80° C. for 2.5 hr
  3. stirringby stirring for 10 hr
  4. filtrationThe precipitated solid was collected by filtration
  5. washthe resultant solid was washed with water
  6. customThis solid was dried under hot air at 100° C. for 24 hr

Sources & evidence

ORD record
ord-1037a0f71dab4a3495ad7589bbae9ccc
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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