Sodium Hydroxide → 6-Amino-3'-trifluoromethyl-[2,2']bipyridinyl-5-carboxylic acid amide

HRID 2054330Notes

Reaction equation

HRID 2054330 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]#[N:19].[OH-:20].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:18]([NH2:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 462029106-Amino-3'-trifluoromethyl[2,2']bipyridinyl-5-carbonitrile

Product 1

HCID 596557626-Amino-3'-trifluoromethyl-[2,2']bipyridinyl-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Cool concentrated sulfuric acid (120 mL) in an ice bath under nitrogen atmosphere. Add in portions 6-amino-3′-trifluoromethyl[2,2′]bipyridinyl-5-carbonitrile (19.8 g) over a period of 15 minutes. Stir at room temperature 48 hours. Pour the reaction mixture over ice, adjust the pH to 10 using 10 N aqueous NaOH, filter the solid, wash the solid with water and dry under vacuum to give 6-amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carboxylic acid amide as a light pink solid.

Workup

  1. additionPour the reaction mixture over ice
  2. filtrationfilter the solid
  3. washwash the solid with water
  4. customdry under vacuum

Sources & evidence

ORD record
ord-34f854ae148a4f7ba8f38693098af3d2
Source dataset
uspto-grants-2008_02
Patent number
US07329664B2

Reaction notes

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