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

HRID 388517Notes

Reaction equation

HRID 388517 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5](O)=[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]([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 685037274-(4-Amino-2,5-difluorophenyl)pyridine-2-carboxamideYield 78.6%

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 stream, and potassium tert-butoxide (4.05 g) was added at room temperature, and the mixture was stirred for 25 minutes. 4-Chloropyridine-2-carboxamide (2.70 g) was added to the mixture, which was stirred at 80° C. for 2.5 hours. The reaction mixture was allowed to cool down to room temperature, and a 1N aqueous solution of sodium hydroxide (74.25 ml) was added, and the mixture was stirred for 10 hours. The precipitated solid was collected by filtration, and the resultant solid was washed with water. The solid was dried by hot air at 100° C. for 24 hours to give the title compound (3.38 g, 74%) as purple powder.

Workup

  1. additionwas added at room temperature
  2. stirringwas stirred at 80° C. for 2.5 hours
  3. stirringthe mixture was stirred for 10 hours
  4. filtrationThe precipitated solid was collected by filtration
  5. washthe resultant solid was washed with water
  6. customThe solid was dried by hot air at 100° C. for 24 hours

Sources & evidence

ORD record
ord-990327e01a054009a4d1ee6a72938531
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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