2-(2-Nitrophenyl)pyridine → 2-(Pyridin-2-yl)aniline

HRID 1006390Notes

Reaction equation

HRID 1006390 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-])=O.[BH4-].[Na+]>C(O)C.S([O-])([O-])(=O)=O.[Cu+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH2:13]

Participants

5

Reactant 2

HCID 2316022-(2-Nitrophenyl)pyridineHCID 4311764Sodium borohydride

Product 1

HCID 4595162-(Pyridin-2-yl)anilineYield 47.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Procedure

Next, 0.96 g (4.8 mmols) of the ortho-(2-pyridyl)nitrobenzene, 0.072 g (0.48 mmol) of copper sulfate and 0.91 g (24.0 mmols) of sodium borohydride were suspended in 30 ml of ethyl alcohol and allowed to react at room temperature. After 5 hours from the start of the reaction, the reaction mixture was filtered through celite, 50 ml of ether was added to the filtrate, the organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The liquid thus obtained was purified by column chromatography and concentrated to give 0.38 g (2.26 mmoles, 47%) of ortho-(2-pyridyl)aniline as a brown liquid.

Workup

  1. customto react at room temperature
  2. customAfter 5 hours from the start of the reaction
  3. filtrationthe reaction mixture was filtered through celite, 50 ml of ether
  4. additionwas added to the filtrate
  5. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe liquid thus obtained
  9. customwas purified by column chromatography
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f687902e56ad4dd48b9c1ae8666bc775
Source dataset
uspto-grants-2004_09
Patent number
US06790540B2

Reaction notes

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