Methanol → 4-N-phenylpyridine-3,4-diamine

HRID 257419Notes

Reaction equation

HRID 257419 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].CO>C(O)C.ClCCl.[C].[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 6120053-nitro-N-phenylpyridin-4-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 105836754-N-phenylpyridine-3,4-diamineYield 88.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Phenylamino-3-nitropyridine (1.40 g, 6.51 mmol) was dissolved in the mixed solvent of 15 ml of ethanol and 10 ml of dichloromethane. After the atmosphere was replaced with nitrogen, 0.10 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 about 15 hours. 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=2:1 (v/v)]to obtain 1.07 g of a light brown solid (yield: 88.7%).

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

Sources & evidence

ORD record
ord-e2ca66bd9d1f4dad92e194a3be04011f
Source dataset
uspto-grants-1993_11
Patent number
US05262415

Reaction notes

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