2-Chloro-3-nitropyridine → 3-Nitro-2-vinylpyridine

HRID 1784877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784877
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([Sn](CCC)(CCC)C=C)[CH2:12]C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N+:8]([C:7]1[C:2]([CH:11]=[CH2:12])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 2

HCID 796132-Chloro-3-nitropyridineHCID 21909134Tripropyl-vinyl-stannane

Produkt 1

HCID 118296173-Nitro-2-vinylpyridineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 0.92 g (5.80 mmol) of 2-chloro-3-nitro-pyridine, 1.60 g (5.80 mmol) tripropyl-vinyl-stannane, 0.335 g (0.290 mmol) Pd(PPh3)4 and 10 mL of toluene were combined and refluxed under an inert atmosphere overnight. After routine aqueous workup the crude product was purified by chromatography on silica gel to give 0.470 g (54% yield) of 3-nitro-2-vinyl-pyridine.

Aufarbeitung

  1. temperaturerefluxed under an inert atmosphere overnight
  2. customAfter routine aqueous workup the crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4582bbaa9e704aacbe4a92fcf7710903
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504401B2

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