4-Nitro-2-(trifluoromethyl)pyridine 1-oxide → 2-(Trifluoromethyl)pyridin-4-amine

HRID 1810990Notes

Reaction equation

HRID 1810990 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-])=O>CCO.[Pd]>[F:14][C:11]([F:12])([F:13])[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 103529914-Nitro-2-(trifluoromethyl)pyridine 1-oxide

Product 1

HCID 102613882-(Trifluoromethyl)pyridin-4-amineYield 74.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-nitro-2-trifluoromethyl-pyridine 1-oxide (0.4 g, 1.90 mmol) in EtOH (15 mL) is added 10% Pd—C (0.04 g) under nitrogen atmosphere. Hydrogenation is performed in a Parr shaker at 30 psi for 3 h at room temperature. After completion of reaction it is filtered through diatomaceous earth and washed with EtOH. Filtrate is concentrated to give 2-trifluoromethyl-pyridin-4-ylamine as a thick liquid (0.23 g, 74%).

Workup

  1. customAfter completion of reaction it
  2. filtrationis filtered through diatomaceous earth
  3. washwashed with EtOH
  4. concentrationFiltrate is concentrated

Sources & evidence

ORD record
ord-2e63ca679f9c436e90ad2feb6e9c67a5
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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