Sodium Hydroxide → HCID 61678566, compound

HRID 388496Notes

Reaction equation

HRID 388496 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-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19](C(N)=O)[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]=[CH:19][CH:18]=2)=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 3035434-Chloropyridine-2-carboxamideHCID 27359194-Amino-3-fluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 61678566HCID 61678566, compoundYield 90.2%

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 stream, potassium tert-butoxide (5.6 g) was added at room temperature, and the reaction mixture was stirred for 15 minutes. 4-Chloropyridine-2-carboxamide (5.0 g) was added to the reaction mixture, followed by stirring in an oil bath at 80° C. (external temperature) under a nitrogen stream for 50 minutes. The reaction mixture was allowed to cool down to room temperature. A 1N aqueous solution of sodium hydroxide (85.5 ml) was added to the reaction mixture, followed by stirring. The precipitated solid was collected by filtration and washed with water. The residue was dried under aeration and then dried by hot air at 100° C. to give the title compound (5.88 g, 74.3%) as pale brown powder.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring in an oil bath at 80° C. (external temperature) under a nitrogen stream for 50 minutes
  3. stirringby stirring
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customThe residue was dried under aeration
  7. customdried by hot air at 100° C.

Sources & evidence

ORD record
ord-501af2f5973f4c31a0d4782c8166f942
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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