Sodium Chloride → 2-(2-Nitrophenyl)pyridine

HRID 1006389Notes

Reaction equation

HRID 1006389 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1I)([O-:22])=[O:21].[Cl-].[Na+]>O1CCCC1>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 69115o-IodonitrobenzeneHCID 6077842-(Tributylstannyl)pyridine

Product 1

HCID 2316022-(2-Nitrophenyl)pyridineYield 24.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction of 8.0 g (0.022 mole) of 2-tributylstannylpyridine with 4.92 g (0.020 mole) of ortho-nitroiodobenzene was carried out in the presence of 0.70 g (0.001 mole) of dichlorobis(triphenlylphosphine)palladium in 100 ml of tetrahydrofuran at 110° C. After 24 hours from the start of the reaction, a saturated aqueous sodium chloride solution was added to the reaction mixture and the reaction product was extracted with ether. The ether layer was then washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated. The resulting liquid was purified by column chromatography and concentrated to give 0.96 g (0.0048 mole, 24.9%) of ortho-(2-pyridyl)nitrobenzene as brown liquid.

Workup

  1. customAfter 24 hours from the start of the reaction
  2. extractionthe reaction product was extracted with ether
  3. washThe ether layer was then washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting liquid was purified by column chromatography
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ed1ddb91cbe44ed98f0ade865cfbd0ee
Source dataset
uspto-grants-2004_09
Patent number
US06790540B2

Reaction notes

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