Sodium Hydroxide → 2-Amino-4(3-trifluoromethyl-pyridin-2-yl)-benzo-nitrile

HRID 968576Notes

Reaction equation

HRID 968576 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>Cl>[NH2:1][C:4]1[CH:11]=[C:10]([C:12]2[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 220300632-Nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To an ice-water cooled solution of 2-nitro-4-(3-trifluoromethyl-pyridin-2-yl)-benzonitrile (0.44 mmol) in conc. HCl (6 mL) add SnCl2 (1.457 mmol). Stir the mixture 2 h at room temperature. neutralize with NaOH, extract with EtOAc, dry over Na2SO4, and concentrate under vacuum. Purify the residue by flash chromatography (4:1 hexanes/EtOAc) to give 2-amino-4-(3-trifluoromethyl-pyridin-2-yl)-benzo-nitrile.

Workup

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

Sources & evidence

ORD record
ord-32b131b615f74886a99b4fcd4c5ae2be
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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