2-Chloro-5-nitro-3-(trifluoromethyl)pyridine → 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

HRID 2403635Notes

Reaction equation

HRID 2403635 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1>O1CCCC1.[Ni]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:12])=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 135322446-Chloro-5-(trifluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Chloro-5-nitro-3-(trifluoromethyl)pyridine 4 (1.57 g, 6.93 mmol) is dissolved in tetrahydrofuran (THF) (10 ml) and added to a suspension of Raney-Ni (200 mg) in THF (20 ml). Hydrogen gas is slowly bubbled through the stirred solution for 24 hours using a balloon. The mixture is filtered through Celite® (available from World Minerals, Inc., Lompoc, Calif.) and the solvent is removed under reduced pressure to obtain 6-chloro-5-(trifluoromethyl)pyridin-3-amine 5.

Workup

  1. customHydrogen gas is slowly bubbled through the stirred solution for 24 hours
  2. filtrationThe mixture is filtered through Celite® (available from World Minerals, Inc., Lompoc, Calif.)
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-2afeaa9125174c008ed509e896a0e23a
Source dataset
uspto-grants-2014_08
Patent number
US08802689B2

Reaction notes

Loading…