N,N,4-Trimethyl-5-nitropyridin-2-amine → N2,N2,4-trimethylpyridine-2,5-diamine

HRID 1398859Notes

Reaction equation

HRID 1398859 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1>C(O)C.[Pd]>[CH3:13][N:2]([CH3:1])[C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([NH2:10])=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 21857174N,N,4-Trimethyl-5-nitropyridin-2-amine

Product 1

HCID 22136281N2,N2,4-trimethylpyridine-2,5-diamineYield 119.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N,N,4-trimethyl-5-nitropyridin-2-amine (15.7 g, 86.6 mmol) in ethanol (200 ml) was added 10% palladium on carbon (50% wet, 1.57 g), and the mixture was purged with hydrogen and stirred under balloon pressure hydrogen at room temperature for 2 days. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound as a brown solid (15.7 g), which was used next reaction without purification.

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-5a655849ed2d497aa32f9b8103bee117
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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