Dimethylcarbamoyl Chloride → 2-Cyano-4-methylpyridine

HRID 499387Notes

Reaction equation

HRID 499387 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-])=[CH:4][CH:3]=1.C[Si]([C:13]#[N:14])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:13]([C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]=1)#[N:14]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 138574-Picoline N-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 887392-Cyano-4-methylpyridineYield 42.1%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

4-Methylpyridine N-oxide (2.0 g, 18.3 mmol) was dissolved in nitroethane (25 ml), and trimethylsilyl cyanide (2.0 g, 20.2 mmol) and N,N-dimethylcarbamoyl chloride (1.7 ml, 18.5 mmol) were added thereto. The reaction mixture was stirred at room temperature for 5 days, 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 obtained crystals were collected by filtration, washed with diisopropyl ether and dried to give the titled compound (0.91 g, 42%).

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. filtrationThe obtained crystals were collected by filtration
  7. washwashed with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-4046feda4b7848c8a5cb314d9489cbfd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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