N,N,6-trimethyl-5-nitropyridin-2-amine → N2,N2,6-trimethylpyridine-2,5-diamine

HRID 1398861Notes

Reaction equation

HRID 1398861 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([CH3:12])[N:4]=1>O1CCCC1.[Pd]>[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH3:12])[N:4]=1

Participants

4

Reactant 1

HCID 59613085N,N,6-trimethyl-5-nitropyridin-2-amine

Product 1

HCID 20748032N2,N2,6-trimethylpyridine-2,5-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N,6-trimethyl-5-nitropyridin-2-amine (2.73 g, 15.1 mmol) in tetrahydrofuran (50 mL) was added 10% palladium on carbon (50% wet, 273 mg), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 14 hr. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound as a brown solid (2.30 g, 15.1 mmol).

Workup

  1. customthe mixture was purged with hydrogen
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0c47b4cebc9044bbaced7217322c58ff
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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