4-Methyl-5-nitro-2-(trifluoromethyl)pyridine → 4-Methyl-6-(trifluoromethyl)pyridin-3-amine

HRID 604638Notes

Reaction equation

HRID 604638 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1>CCO.[Pt]=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:12])[F:13])[N:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 534142754-Methyl-5-nitro-2-(trifluoromethyl)pyridine

Product 1

HCID 497579514-Methyl-6-(trifluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A suspension of platinum oxide (36.9 mg) in a solution of 4-methyl-5-nitro-2-(trifluoromethyl)pyridine (369.4 mg, 0.162 mmol) in EtOH (12.7 mL) was stirred under a balloon of H2 for 5½ h. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford 4-methyl-6-(trifluoromethyl)pyridin-3-amine. LCMS calc.=177.1; found=177.1 (M+1)+. 1H NMR (600 MHz, CDCl3): δ 8.04 (s, 1H); 7.27 (s, 1H); 4.28 (s, 2H); 2.15 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8498858c1d0d4203bf9c1459721a6dba
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

Loading…