3-Methyl-5-nitro-2-[4-(trifluoromethyl)phenyl]pyridine → HCID 67153606, compound

HRID 2406948Notes

Reaction equation

HRID 2406948 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 671534333-Methyl-5-nitro-2-[4-(trifluoromethyl)phenyl]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 67153606HCID 67153606, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-methyl-5-nitro-2-(4-(trifluoromethyl)phenyl)pyridine (223 mg, 0.79 mmol) in ethanol (30 mL) was added 10 wt % palladium on carbon (100 mg). The reaction was pressurized to 50 psi hydrogen and was stirred at room temperature for 3 hours. The reaction mixture was filtered through Celite and concentrated to give 5-methyl-6-(4-(trifluoromethyl)phenyl)pyridin-3-amine (198 mg, 99%). 1H NMR (400 MHz, CDCl3, δ): 8.04 (s, 1 H), 7.67 (m, 2 H), 7.60 (m, 2 H), 6.91 (s, 1 H), 3.72 (br s, 2 H), 2.30 (s, 3 H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5ee132f551824713b097eae50b2008b9
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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