Dimethylcarbamoyl Chloride → 5-Acetyl-2-cyanopyridine

HRID 499398Notes

Reaction equation

HRID 499398 reaction equation
[C:1]([C:4]1[CH:5]=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:15]#[N:16])=[N:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 1233381-(1-Oxido-3-pyridinyl)ethanone

Product 1

HCID 121756775-Acetyl-2-cyanopyridineYield 21%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

3-Acetylpyridine N-oxide (2.0 g, 14.6 mmol) was dissolved in nitroethane (20 ml), and trimethylsilyl cyanide (1.7 g, 16.7 mmol) and N,N-dimethylcarbamoyl chloride (1.8 g, 16.7 mmol) were added thereto. The reaction mixture was stirred at room temperature for 16 hrs, concentrated under reduced pressure, combined with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (0.40 g, 21%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-bdce8e9ea0994199ab033252f7fc52f8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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