Triethylamine → 3-Chloropyridine-2-carbonitrile

HRID 502598Notes

Reaction equation

HRID 502598 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 8182583-Chloropyridine-2-carbonitrileYield 84.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d6467b72557b4382aff3956d0bcd526e
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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