Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

HRID 1784939Notes

Reaction equation

HRID 1784939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N+:6]([O-])=[CH:5][CH:4]=1.[Si]([C:14]#[N:15])(C)(C)C.CN(C)C(Cl)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:14]#[N:15])[CH:4]=1

Participants

7

Reactant 4

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

Product 1

HCID 134151564-Methoxypyridine-2-carbonitrileYield 73.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of 1.2 g (9.67 mmol) of 4-methoxypyridine-N-oxide in 18 mL of CH2Cl2 at r.t. was added 1.6 mL (12.0 mmol) of TMSCN. After 5 min. 0.9 mL (9.8 mmol) of dimethylcarbamoyl chloride. The solution was stirred at r.t. for 13 h and CHCl3 and 20 mL of 10% K2CO3 was added. The aqueous layer was extracted with CHCl3 3 times, and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (38-44% EtOAc/hexanes) provided 949 mg of 4-methoxypicolinonitrile as a colorless solid in 73% yield.

Workup

  1. extractionThe aqueous layer was extracted with CHCl3 3 times
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash silica gel chromatography (38-44% EtOAc/hexanes)

Sources & evidence

ORD record
ord-899b98d2ab484400b7bea25123e46ab5
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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