Ethyl Acetate → 5-Acetyl-2-cyanopyridine

HRID 571689Notes

Reaction equation

HRID 571689 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([Cu])#[N:12].CCOC(C)=O>CN(C=O)C.O>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([C:11]#[N:12])=[N:7][CH:6]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 156681955-Acetyl-2-bromopyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 121756775-Acetyl-2-cyanopyridineYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-(6-bromopyridin-3-yl)ethanone (200 mg, 1.0 mmol) and CuCN (179 mg, 2.0 mmol) in anhydrous DMF (5 mL) was heated at 110° C. for 18 h under N2. The mixture was cooled to room temperature and diluted with water. After addition of EtOAc and filtration, the aqueous layer was extracted with EtOAc. The organic layer was washed with sat. NaHCO3 (aq), brine, and then dried (MgSO4) and concentrated. The product 5-acetylpicolinonitrile (120 mg) was obtained by silica gel chromatography (elution with 0-20% EtOAc/Hex).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with sat. NaHCO3 (aq), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82ce45ade4f349ba9e5720221e9ebbb2
Source dataset
uspto-grants-2015_05
Patent number
US09029362B2

Reaction notes

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