4-Picoline N-oxide → 2-Cyano-4-methylpyridine

HRID 1352983Notes

Reaction equation

HRID 1352983 reaction equation
[N+:1]1([O-])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C[Si]([C:13]#[N:14])(C)C.N12CCCN=C1CCCCC2>C1COCC1>[C:13]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=1)#[N:14]

Participants

5

Reactant 3

HCID 138574-Picoline N-oxideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 887392-Cyano-4-methylpyridineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 4-picoline N-oxide (13.64 g, 0.124 mole) in 82 ml of THF, under an inert atmosphere, was added trimethylsilyl cyanide (20.1 ml, 0.15 mole) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.4 ml, 0.028 mole). After stirring at 25° C. for 12 hours, the reaction mixture was heated to reflux. After 4.5 hours, the solvent was removed under reduced pressure and the crude sample was eluted with methylene chloride through a pad of Florisil®. The solvent was removed under reduced pressure to provide (8.7 g, 60%) of 2-cyano-4-methyl pyridine, a white crystalline solid: mp 88–89° C. Anal. Calc'd. for C7H6N2: C, 71.17; H, 5.12; N, 23.71. Found: C, 70.17; H, 5.12; N, 23.44.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter 4.5 hours
  3. customthe solvent was removed under reduced pressure
  4. washthe crude sample was eluted with methylene chloride through a pad of Florisil®
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-54f6f4f749694e59a3edf4300f922eb7
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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