Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

HRID 379769Notes

Reaction equation

HRID 379769 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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:14]#[N:15])[CH:4]=1

Participants

6

Reactant 4

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

Product 1

HCID 134151564-Methoxypyridine-2-carbonitrileYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-methoxypiridine-N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cyanide (4.84 g, 46.3 mmol) in dichloromethane (60 ml) cooled to 0° C. was added dropwise N,N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol). The mixture was allowed to warm to ambient temperature and stirred for 16 h. The mixture was cooled to 0° C. and a 30% aqueous solution of K2CO3 (100 ml) was added. The crude product was extracted with dichloromethane (100 ml×2), the organic extracts dried (MgSO4) and evaporated to give 4-methoxy-2-pyridinecarbonitrile (5.35 g, 100%). 1H-NMR (CDCl3) δ: 8.51 (1 H, d, J=5.9 Hz), 7.22 (1 H, d, J=2.6 Hz), 7.01 (1 H, dd, J=2.6, 5.9 Hz), 3.91 (3H, s)

Workup

  1. temperatureto warm to ambient temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. extractionThe crude product was extracted with dichloromethane (100 ml×2)
  4. dry with materialthe organic extracts dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5c5e149d18714744a125204ab58d5042
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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