Sulfuric Acid → 3-Phenoxy-5-(trifluoromethyl)picolinamide

HRID 1809598

Reaction equation

HRID 1809598 reaction equation
[O:1]([C:8]1[C:9]([C:18]#[N:19])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21].[OH-].[NH4+]>>[O:1]([C:8]1[C:9]([C:18]([NH2:19])=[O:21])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 674852863-Phenoxy-5-(trifluoromethyl)picolinonitrile

Product 1

HCID 674866453-Phenoxy-5-(trifluoromethyl)picolinamideYield 84.3%

Procedure

3-Phenoxy-5-(trifluoromethyl)picolinonitrile (0.190 g, 0.719 mmol) was combined with 2 ml of sulfuric acid and agitated for 3 hours. Ice was added to the mixture, and the solution was basified with ammonium hydroxide solution. The resulting slurry was filtered and solids washed with water and dried in the air to afford 3-phenoxy-5-(trifluoromethyl)picolinamide (0.171 g, 84.3% yield) as a white solid.

Workup

  1. additionIce was added to the mixture
  2. filtrationThe resulting slurry was filtered
  3. washsolids washed with water
  4. customdried in the air

Sources & evidence

ORD record
ord-370172ece5634327b70de642dfe49b82
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Linked notes

Loading…