N,N-dimethyl-6-nitropyridin-3-amine → N5,N5-Dimethylpyridine-2,5-diamine

HRID 645377

Reaction equation

HRID 645377 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[N:5][C:6]([N+:9]([O-])=O)=[CH:7][CH:8]=1>C(O)C>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[N:5][CH:4]=1

Participants

3

Reactant 1

HCID 21897368N,N-dimethyl-6-nitropyridin-3-amine

Product 1

HCID 5743468N5,N5-Dimethylpyridine-2,5-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The N,N-dimethyl-6-nitropyridine-3-amine obtained above is taken up in 25 ml of ethanol. After addition of 4.8 g of stannous chloride, the reaction mixture is heated at reflux for 30 minutes and then concentrated to dryness. The residue is chromatographed on a column of silica (40-63 μm), elution being carried out with a mixture of dichloromethane and ammoniacal methanol (90/10). The fractions comprising the expected product are combined and concentrated to give 750 mg of 5-dimethylaminopyridine-2-amine in the form of a pasty yellow solid.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 30 minutes
  3. concentrationconcentrated to dryness
  4. customThe residue is chromatographed on a column of silica (40-63 μm), elution
  5. additionbeing carried out with a mixture of dichloromethane and ammoniacal methanol (90/10)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0d3391d71d19420b8014b85f19f742cb
Source dataset
uspto-grants-2010_04
Patent number
US07704989B2

Linked notes

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