3,5-Dichloropyridine → HCID 22724426, compound

HRID 2086829Notes

Reaction equation

HRID 2086829 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-:3])=[O:2].[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](Cl)[CH:18]=1.C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](/[CH:8]=[CH:7]/[C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 171533,5-DichloropyridineHCID 685143-NitrostyreneHCID 516892Sodium Bicarbonate2×

Product 1

HCID 22724426HCID 22724426, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3-nitrostyrene (3.98 g), 3,5-dichloropyridine (3.70 g), palladium(II) acetate (0.20 g), tetrabutylammonium chloride (7.0 g) and sodium bicarbonate (5.3 g) in N,N-dimethylformamide (35 ml) was stirred at 135° C. for 2 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-chloro-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine (3.01 g).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-0f6621f3c2bf4a41a7efeb1f0160e848
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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