2-Pyridinamine, N-methyl-5-nitro-N-(2,2,2-trifluoroethyl)- → 2,5-Pyridinediamine, N2-methyl-N2-(2,2,2-trifluoroethyl)-

HRID 2236169Notes

Reaction equation

HRID 2236169 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][N:9]=1)[CH2:3][C:4]([F:7])([F:6])[F:5]>C(O)C.[Pd]>[CH3:1][N:2]([CH2:3][C:4]([F:7])([F:5])[F:6])[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][N:9]=1

Participants

4

Reactant 1

HCID 675372732-Pyridinamine, N-methyl-5-nitro-N-(2,2,2-trifluoroethyl)-

Product 1

HCID 593013052,5-Pyridinediamine, N2-methyl-N2-(2,2,2-trifluoroethyl)-Yield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl-(5-nitro-pyridin-2-yl)-(2,2,2-trifluoro-ethyl)-amine (80 mg, 0.34 mmol) in ethanol (10 mL) in the presence of 10% palladium on carbon (10 mg) was shaken under hydrogen with a pressure of 50 psi at room temperature for 2 hours. After the reaction was complete, the reaction mixture was filtered through a plug of celite and the filtration pad was washed with ethanol. The organic layers were combined and concentrated to give N2-methyl-N2-(2,2,2-trifluoro-ethyl)-pyridine-2,5-diamine (70 mg, crude) as a brown oil, which was directly used in the next step without further purification. LCMS calcd for C8H10F3N3 (m/e) 205, obsd 206 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered through a plug of celite
  2. washthe filtration pad was washed with ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-40700f0ab0fb466ea4997895bf990fa0
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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