Potassium Carbonate → 2-Methyl-3-nitropyridine

HRID 362623

Reaktionsgleichung

Reaktionsgleichung von HRID 362623
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11]B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:11][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 139377Methylboronic Acid

Produkt 1

HCID 3293602-Methyl-3-nitropyridineAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-3-nitropyridine 1 (793 mg, 5.0 mmol), methylboronic acid (329 mg, 5.5 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol) and K2CO3 (2.073 g, 15.0 mmol) in dioxane (25 mL) was refluxed for 2 days. It was then cooled to room temperature and filtered. The solvent was removed and the residue was isolated by flash chromatography (50% ethyl acetate in hexanes) to provide 623 mg (90%) of 2-methyl-3-nitropyridine 3.

Aufarbeitung

  1. temperaturewas refluxed for 2 days
  2. filtrationfiltered
  3. customThe solvent was removed
  4. customthe residue was isolated by flash chromatography (50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-469fc6e1ae89416eac8e30426cebd3ef
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869676

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