Triethylamine → 4-Methoxypyridine-2-carbonitrile

HRID 1437205Notes

Reaction equation

HRID 1437205 reaction equation
[CH2:1]([N:3](CC)CC)C.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=1.C[Si](C#N)(C)C>C(#N)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:1]#[N:3])[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 707434-Methoxypyridine N-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 134151564-Methoxypyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In an argon atmosphere, triethylamine (17.8 mL) was added to 4-methoxypyridine-N-oxide (8.0 g) in acetonitrile (160 mL) at room temperature. Trimethylsilyl cyanide (24.1 mL) was added dropwise to the mixture, followed by stirring for 20 minutes. Subsequently, the mixture was stirred at 95° C. for 14 hours, and then cooled in air. The solvent was evaporated under reduced pressure. The residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate. The organic layer was dried over sodium hydrogensulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid substance (1.57 g, 18%).

Workup

  1. stirringSubsequently, the mixture was stirred at 95° C. for 14 hours
  2. temperaturecooled in air
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was partitioned between saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  5. dry with materialThe organic layer was dried over sodium hydrogensulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2b658a2fcc2247f19b6a67628c5b1534
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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