Sodium Hydroxide → 4-(4-Amino-3-fluorophenoxy)pyridine-2-carboxamide

HRID 2066251Notes

Reaction equation

HRID 2066251 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CC(C)([O-:13])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][NH-:24])[CH:18]=1.[OH-].[Na+]>CS(C)=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]([NH2:24])=[O:13])[CH:18]=2)=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27359194-Amino-3-fluorophenolHCID 23665647Potassium tert-butoxideHCID 866258584-Chloropicolylamide

Product 1

HCID 231534864-(4-Amino-3-fluorophenoxy)pyridine-2-carboxamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Amino-3-fluorophenol (5.7 g) was dissolved in dimethyl sulfoxide (57 ml) under a nitrogen atmosphere, and potassium tert-butoxide (5.6 g) was added at room temperature, followed by stirring for 15 min. To the reaction mixture was added 4-chloropicolylamide (5.0 g), followed by stirring in an oil bath at an external temperature of 80° C. under a nitrogen atmosphere for 50 min. The reaction mixture was allowed to cool down to room temperature. To the reaction mixture was added a 1N aqueous solution of sodium hydroxide (85.5 ml), followed by stirring. The precipitated solid was collected by filtration, and washed with water. The solid was dried under aeration, then hot air-dried at 100° C. to provide the titled compound as pale brown powder (5.88 g, 74.3%).

Workup

  1. stirringby stirring in an oil bath at an external temperature of 80° C. under a nitrogen atmosphere for 50 min
  2. stirringby stirring
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customThe solid was dried under aeration
  6. customhot air-dried at 100° C.

Sources & evidence

ORD record
ord-6146a633df1e46cc92bdd53b67af01ec
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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