Sodium Hydroxide → 4-(4-Amino-2-fluorophenoxy)picolinamide

HRID 2265678Notes

Reaction equation

HRID 2265678 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:25])=[O:24])[CH:18]=1.[OH-].[Na+]>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH2:25])=[O:24])[CH:18]=2)=[C:4]([F:9])[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 3035434-Chloropyridine-2-carboxamideHCID 2735918Phenol, 4-amino-2-fluoro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 231532054-(4-Amino-2-fluorophenoxy)picolinamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

4-Amino-2-fluorophenol (9.63 g) was dissolved in dimethyl sulfoxide (100 ml) under a nitrogen atmosphere. Potassium tert-butoxide (9.07 g) was added at room temperature, followed by stirring for 15 min. 4-Chloropyridine-2-carboxamide (7.9 g) was added thereto, followed by stirring at 80° C. under a nitrogen atmosphere for 1 hr. The reaction mixture was allowed to cool down to room temperature. To the reaction mixture was added a 1N aqueous solution of sodium hydroxide (100 ml), then water (100 ml), followed by stirring for 5 hr. The precipitated solid was collected by filtration with suction, and washed with water (50 ml, 4 times). The resultant solid was hot air-dried at 60° C. for 2 days to provide the titled compound as pale brown powder (10.39 g, 83%).

Workup

  1. stirringby stirring at 80° C. under a nitrogen atmosphere for 1 hr
  2. stirringby stirring for 5 hr
  3. filtrationThe precipitated solid was collected by filtration with suction
  4. washwashed with water (50 ml, 4 times)
  5. customThe resultant solid was hot air-dried at 60° C. for 2 days

Sources & evidence

ORD record
ord-2e5ba91f17614ccc984fb68344efe947
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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