Triethylamine → HCID 58997212, compound

HRID 251062Notes

Reaction equation

HRID 251062 reaction equation
[Cl:1][C:2]1[N+:7]([O-])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH3:13].C[Si]([C:18]#[N:19])(C)C.CCN(CC)CC.C([O-])(O)=O.[Na+]>CC#N>[Cl:1][C:2]1[N:7]=[C:6]([C:18]#[N:19])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 58996948HCID 58996948, compound

Product 1

HCID 58997212HCID 58997212, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-chloro-5-methyl-3-trifluoromethyl-pyridine-1-oxide (1.03 g, 5.30 mmol), trimethylsilyl cyanide (1.57 g, 16.0 mmol) and Et3N (1.34 g, 13.3 mmol) in dry CH3CN (30 mL) was heated at reflux for 64 h. The reaction mixture was then cooled to room temperature, and saturated aqueous NaHCO3 (20 mL) was added. After concentrated under reduced pressure the mixture was extracted with CH2Cl2 (3×30 mL). The extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (6:1 hexanes/EtOAc) to afford 6-chloro-5-methyl-3-trifluoromethyl-pyridine-2-carbonitrile as a colorless oil (0.660 g, 56%). 1H NMR (CDCl3) δ 2.56 (s, 3H), 7.95 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 64 h
  3. concentrationAfter concentrated under reduced pressure the mixture
  4. extractionwas extracted with CH2Cl2 (3×30 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed by evaporation under vacuum
  8. customthe residue was purified by flash chromatography on a silica gel column (6:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-31c312de1ba24a4896ddc8e5dbb87634
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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