Water → 2-Ethenyl-5-nitropyridine

HRID 2262604Notes

Reaction equation

HRID 2262604 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC.O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:11]=[CH2:12])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 783082-Chloro-5-nitropyridineHCID 81998Tributylvinyltin

Product 1

HCID 230905502-Ethenyl-5-nitropyridineYield 111.6%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 1140TolueneSolvent

Procedure

0.5 g of 2-chloro-5-nitro-pyridine (3.15 mmol), 1.2 g of tributyl-vinyl-stannane (3.78 mmol), 0.036 g of tetrakistriphenylphosphinpalladium(0) (0.03 mmol), and 0.024 g of triphenylphosphin (0.09 mmol) were dissolved in 20 ml of toluene and stirred for 2 h under reflux. Upon cooling to room temperature, 10 ml of water were added, the aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (10%). Fractions containing the product were combined, the solvent evaporated to yield 0.528 g of the desired product.

Workup

  1. temperatureunder reflux
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (10%)
  8. additionFractions containing the product
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-b7e49e1d7a8c4bd78b33062ea0e82178
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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