Dimethylcarbamoyl Chloride → 5-Methoxy-6-methylpicolinonitrile

HRID 398253

Reaction equation

HRID 398253 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:10])=[N+:5]([O-])[CH:6]=[CH:7][CH:8]=1.[C:11]([Si](C)(C)C)#[N:12].CN(C)C(Cl)=O>ClCCl>[C:11]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:10])[N:5]=1)#[N:12]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 122140163-Methoxy-2-methylpyridine 1-oxide

Product 1

HCID 230024175-Methoxy-6-methylpicolinonitrileYield 11.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution obtained by dissolving 3-methoxy-2-methyl-pyridine-N-oxide (1.57 g, 11.3 mmol) in 30 ml of dichloromethane were added cyanotrimethylsilane (1.12 g, 11.3 mmol) and dimethylcarbamoyl chloride (1.21 g, 11.3 mmol), followed by stirring at room temperature for 9 days. The reaction solution was washed with 10% sodium carbonate aqueous solution and then with water. The organic layer was dried with sodium sulfate and concentrated to remove the solvent, by which 0.198 g (percent yield: 11.8%) of 2-cyano-5-methoxy-6-methylpyridine was obtained.

Workup

  1. customTo a solution obtained
  2. washThe reaction solution was washed with 10% sodium carbonate aqueous solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated
  5. customto remove the solvent

Sources & evidence

ORD record
ord-1d1b1b0466054e788516132c7d0acd6c
Source dataset
uspto-grants-2003_08
Patent number
US06610853B1

Linked notes

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