HCID 18953543, compound → 4-(1H-imidazol-1-yl)pyridin-3-amine

HRID 257417Notes

Reaction equation

HRID 257417 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[N+:12]([O-])=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[H][H]>C(O)C.[C].[Pd]>[NH2:12][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 18953543HCID 18953543, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 189535484-(1H-imidazol-1-yl)pyridin-3-amineYield 91.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

4-(1-Imidazolyl)-3-nitropyridine (2.10 g, 11.0 mmol) was dissolved in 20 ml of ethanol. After the atmosphere was replaced with nitrogen, 0.25 g of 10% palladium-carbon was added thereto. After the atmosphere was replaced with hydrogen, hydrogen addition was conducted with stirring at room temperature for 3 days. Palladium-carbon was removed by filtration and the filtered cake was washed with ethanol. The filtrate and the washings were combined and then concentrated. The residue was purified by silica gel column chromatography [eluent: dichloromethane: methanol=8:1-6:1 (v/v)] to obtain 1.62 g of a light brown solid (yield: 91.6%).

Workup

  1. additionwas added
  2. customPalladium-carbon was removed by filtration
  3. washthe filtered cake was washed with ethanol
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography [eluent: dichloromethane: methanol=8:1-6:1 (v/v)]

Sources & evidence

ORD record
ord-5bff29b70bfc47e88a7c6f72accdcd38
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

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