Triethylamine → HCID 19780237, compound

HRID 2081587Notes

Reaction equation

HRID 2081587 reaction equation
C[Si]([C:5]#[N:6])(C)C.[Cl:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=1[O-].C(N(CC)CC)C>C(#N)C>[Cl:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:5]#[N:6])[N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 19780238HCID 19780238, compound

Product 1

HCID 19780237HCID 19780237, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl cyanide (36.15 g, 48.6 ml, 0.36 moles) was added dropwise to a solution of 2-(o-chlorobenzyl)-pyridine-N-oxide (32.0 g, 0.15 moles) and triethylamine (22.13 g, 30.5 ml, 0.22 moles) in acetonitrile (100 ml) at 20° C. under a nitrogen atmosphere. After complete addition the reaction mixture was heated under reflux for 48 hours, cooled to room temperature and partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic layer was washed with water and saturated sodium chloride solution and was then dried over anhydrous magnesium sulphate. Removal of the solvent gave an orange brown oil which was purified by column chromatography (silica gel eluted with hexane:ethyl acetate 4:1) to give 2-(o-chlorobenzyl)-6-cyanopyridine (11.5 g, 35%) as a pale yellow oil.

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 48 hours
  4. custompartitioned between methylene chloride and saturated sodium bicarbonate solution
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialwas then dried over anhydrous magnesium sulphate
  7. customRemoval of the solvent
  8. customgave an orange brown oil which
  9. customwas purified by column chromatography (silica gel eluted with hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-97d5f16fc7044fb0bb3bbebaa1966990
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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