Sodium Hydroxide → 2-Amino4-(3-trifluoromethyl-pyridin-2-yl)-benzamide

HRID 968579Notes

Reaction equation

HRID 968579 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH-:20].[Na+]>OS(O)(=O)=O>[NH2:1][C:2]1[CH:9]=[C:8]([C:10]2[C:15]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]([NH2:5])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220304962-Amino-4(3-trifluoromethyl-pyridin-2-yl)-benzo-nitrile

Product 1

HCID 220300742-Amino4-(3-trifluoromethyl-pyridin-2-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Stir a mixture of 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzo-nitrile (0.50 mmol) in 70% H2SO4 (10 ml) at 110° C. for 1 hour. Cool to room temperature, neutralize with NaOH, extract with EtOAc, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography (3:2 hexanes/EtOAc) to give 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzamide.

Workup

  1. extractionextract with EtOAc
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate under vacuum
  4. customPurify the residue by flash chromatography (3:2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-34008914c3a84f3486a96cb6c190f2d0
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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