Dimethylcarbamoyl Chloride → 4,5-Dimethylpyridine-2-carbonitrile

HRID 705400Notes

Reaction equation

HRID 705400 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:10][N:11](C)C(Cl)=O.C[Si](C#N)(C)C>C(Cl)Cl>[C:10]([C:5]1[N:4]=[CH:3][C:2]([CH3:1])=[C:7]([CH3:8])[CH:6]=1)#[N:11]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 3024543,4-Dimethylpyridine 1-oxide

Product 1

HCID 132444834,5-Dimethylpyridine-2-carbonitrileYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.8 g of the obtained 3,4-dimethylpyridine-N-oxide (144.5 mmol) was dissolved under an argon gas atmosphere in 250 mL of methylene dichloride, added thereto 13.2 mL of dimethyl carbamoyl chloride (144 mmol), then 19.0 mL of trimethylsilyl cyanide (152 mmol), and stirred overnight at room temperature. The reaction solution was quenched with 10%-K2CO3 aqueous solution, the methylene dichloride layer was separated, dried on salt cake and concentrated to give 3.40 g of 6-cyano-3,4-dimethylpyridine (18% yield).

Workup

  1. additionadded
  2. customThe reaction solution was quenched with 10%-K2CO3 aqueous solution
  3. customthe methylene dichloride layer was separated
  4. customdried on salt cake
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c7130fc8c111404c873fc7fd6081327f
Source dataset
uspto-grants-2015_11
Patent number
US09174906B2

Reaction notes

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