Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 502598

Reaktionsgleichung

Reaktionsgleichung von HRID 502598
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si](C[C:14]#[N:15])(C)C.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:14]#[N:15])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 87557(Trimethylsilyl)acetonitrileHCID 123133Pyridine, 3-chloro-, 1-oxide

Produkt 1

HCID 8182583-Chloropyridine-2-carbonitrileAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-chloropyridine-N-oxide (2.12 g, 16.30 mmol), trimethylsilyl(acetonitrile) (3.25 g, 32.80 mmol), triethylamine (3.30 g, 32.60 mmol) and acetonitrile (10 mL) was heated at reflux for 6 h. After concentration under reduced pressure, the resulting residue was basified with aqueous sodium carbonate (3N) and extracted with methylene chloride. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-chloropicolinonitrile (1.90 g). The crude product was carried forward without further purification. MW=139 confirmed by LC-MS, tr=2.33 min (Method E) MH+=140.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. concentrationAfter concentration under reduced pressure
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d6467b72557b4382aff3956d0bcd526e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776847B2

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