Acetyl chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 556390

Reaction equation

HRID 556390 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:18]#[N:19])(C)C.C(Cl)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:18]#[N:19])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 877584-Phenyl-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenylpyridine N-oxide (5 g) in DCM (50 mL) was added at RT trimethylsilylcyanide (11 mL), followed by acetyl chloride (3.1 mL) over 10 min. The reaction mixture was stirred overnight at RT. A solution of aq. 10% Na2CO3 was added and the mixture was extracted with EA. The combined org. phases were washed with brine, dried (Na2SO4) and evaporated off. Filtration over a plug of silica gel (Hept/EA 1/1) gave the desired compound (450 mg).

Workup

  1. extractionthe mixture was extracted with EA
  2. washphases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated off
  5. filtrationFiltration over a plug of silica gel (Hept/EA 1/1)

Sources & evidence

ORD record
ord-9c430b76a63140548e31507170d80bec
Source dataset
uspto-grants-2011_11
Patent number
US08058263B2

Linked notes

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