Dimethylcarbamoyl Chloride → Methyl 2-cyanopyridine-4-carboxylate

HRID 1635500Notes

Reaction equation

HRID 1635500 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[CH:7]=[CH:6][N+:5]([O-])=[CH:4][CH:3]=1.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:16]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=1)[C:1]([O:10][CH3:11])=[O:9])#[N:17]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 2366364-(Methoxycarbonyl)pyridine 1-oxide

Product 1

HCID 12132796Methyl 2-cyanopyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl isonicotinate N-oxide (20.0 g, 0.26 mol) in 200 mL of methylene chloride was added trimethylsilyl cyanide (16.1 g, 0.32 mol), followed by a solution of dimethylcarbamyl chloride (17.82 g, 0.32 mol) in 50 mL of methylene chloride at room temperature. The reaction mixture was stirred overnight (about eighteen hours) and then treated with 500 mL of 10% potassium carbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to 15.2 g of crude product as a brown solid, which was used without further purification.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 15.2 g of crude product as a brown solid, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-5bbb6645651d498d96cbd6d42e3e507c
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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