Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

HRID 256817Notes

Reaction equation

HRID 256817 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N+:6]([O-])=[CH:5][CH:4]=1.C[Si]([C:14]#[N:15])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:14]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][N:6]=1)#[N:15]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 707434-Methoxypyridine N-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 134151564-Methoxypyridine-2-carbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 4-methoxypyridine N-oxide (50 g, 0.4 mol) was dissolved in dichloromethane (200 mL), and to it was added trimethylsilylcyanide (67.4 mL, 0.506 mol) at room temperature. Dimethylcarbamyl chloride (46.5 mL, 0.506 mol) was added dropwise with stirring to the reaction mixture over a 30-min period. The reaction mixture was stirred at room temperature for 24 hours. A solution of 10% aqueous potassium Carbonate (100 mL) was added dropwise, and stirring was continued for 15 minutes. The organic layer was separated, dried, and concentrated to afford 2-cyano-4-methoxypyridine 1 (51.5 g, 96%) as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 hours
  2. stirringstirring
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab8360f7192d4aa6b50ddc6eb69bd2c5
Source dataset
uspto-grants-1993_11
Patent number
US05260286

Reaction notes

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