Triethylamine → HCID 18953923, compound

HRID 2379815Notes

Reaction equation

HRID 2379815 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][N+:9]([O-])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C[Si](C)(C)[C:15]#[N:16].C(N(CC)CC)C>C(#N)C>[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:15]#[N:16])[CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 12883302N-[(1-Oxo-1lambda~5~-pyridin-4-yl)methyl]acetamide

Product 1

HCID 18953923HCID 18953923, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(acetylaminomethyl)pyridine N-oxide (17.5 g), trimethylsilanecarbonitrile (53 ml) and triethylamine (43 ml) in acetonitrile (180 ml) was refluxed for 7 hours with stirring. After evaporation of the solvent, the residue was diluted with water and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (430 g) by eluting with a mixture of ethyl acetate and methanol (50:1) followed by recrystallization with a mixture of ethyl acetate and diisopropyl ether to give 4-(acetylaminomethyl)-2-pyridinecarbonitrile (8.66 g).

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with water
  3. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (430 g)
  7. washby eluting with a mixture of ethyl acetate and methanol (50:1)
  8. customfollowed by recrystallization with a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-393410b38eff41ab9f51a97d13c2e10f
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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