3-nitro-N-phenylpyridin-4-amine → 4-N-phenylpyridine-3,4-diamine

HRID 1491638Notes

Reaction equation

HRID 1491638 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]>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

6

Reactant 2

HCID 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 6344DichloromethaneSolvent

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: dichloromethane: methanol=2:1 (v/v)]

Sources & evidence

ORD record
ord-37e8568da90f4bd09cec075a126afc53
Source dataset
uspto-grants-1994_12
Patent number
US05371086

Reaction notes

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