Triethylamine → HCID 53763119, compound

HRID 2081582Notes

Reaction equation

HRID 2081582 reaction equation
C[Si]([C:5]#[N:6])(C)C.[Cl:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=2[O-])=[CH:10][CH:9]=1.C(N(CC)CC)C>>[Cl:7][C:8]1[CH:21]=[CH:20][C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:5]#[N:6])[N:14]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 19780249HCID 19780249, compound

Product 1

HCID 53763119HCID 53763119, compoundYield 15%

Procedure

Trimethylsilyl cyanide (12.42 g, 16.7 ml, 0.125 moles) was added dropwise to a solution of 2-p-chlorobenzyl-pyridine-N-oxide (11.0 g, 0.05 moles) and triethylamine (7.61 g, 10.5 ml, 0.075 moles) in acetronitrile (40 ml) at 20° C. After complete addition the mixture was heated under reflux for 48 hours, cooled to room temperature and partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer was washed with water and saturated sodium chloride and dried over anhydrous magnesium sulphate. Removal of the solvent gave a brown oil which was purified by column chromatography (silica gel eluted with hexane:ethyl acetate 9:1) to give 2-p-chlorobenzyl-6-cyanopyridine (1.69 g, 15%) as a pale yellow oil.

Workup

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

Sources & evidence

ORD record
ord-1a8896b686764a23ae5c9ab1f4b81dbd
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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