Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

HRID 1828424Notes

Reaction equation

HRID 1828424 reaction equation
O.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][CH:5]=1.C[Si]([C:15]#[N:16])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OCC)(=O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:15]#[N:16])[CH:5]=1

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanide2×HCID 162122934-Methoxypyridine N-oxide hydrate

Product 1

HCID 134151564-Methoxypyridine-2-carbonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxypyridine-N-oxide hydrate (1 g, 6.99 mmol) dissolved in dichloromethane (4 ml) was added with trimethylsilyl cyanide (1 ml, 7.69 mmol) and subsequently added dropwise with N,N-dimethylcarbamoyl chloride (0.8 ml, 9.09 mmol) under ice cooling. The reaction solution was warmed to room temperature, stirred for 1 hour, and then added further with trimethylsilyl cyanide (0.2 ml, 1.40 mmol). The reaction solution was stirred for 19 hours, then added with 10% potassium carbonate (2 ml). The mixture was diluted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting crystals were washed with hexane to obtain 560 mg (60%) of the title compound as pink crystals without purification.

Workup

  1. stirringThe reaction solution was stirred for 19 hours
  2. washwashed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-c006f6aa16db485aa6f55bd994283c68
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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