2-Vinylpyridine → 2-(m-Nitrostyryl)pyridine

HRID 2230961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230961
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH2:12].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>[N+:8]([C:4]1[CH:3]=[C:2](/[CH:12]=[CH:11]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Komponenten

7

Edukt 3

HCID 75212-VinylpyridineHCID 125741-Iodo-3-nitrobenzeneHCID 516892Sodium Bicarbonate2×

Produkt 1

HCID 53764932-(m-Nitrostyryl)pyridineAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 1-iodo-3-nitrobenzene (7.47 g), 2-vinylpyridine (4.73 g), palladium(II) acetate (0.20 g), tetrabutylammonium chloride (8.34 g) and sodium bicarbonate (6.3 g) in N,N-dimethylformamide (50 ml) was stirred at 110° C. for 5 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 2-[(E)-2-(3-nitrophenyl)vinyl]pyridine (3.37 g).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-838528988f234ac7b4b23e276ec94eb3
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06426345B1

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