6-Bromo-3-pyridinecarboxaldehyde → 5-Formylpyridine-2-carbonitrile

HRID 1429692Notes

Reaction equation

HRID 1429692 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[C:10]([Cu])#[N:11]>CN(C=O)C.CCOC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:10]#[N:11])=[N:3][CH:4]=1)=[O:7]

Participants

5

Reactant 2

HCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 109862635-Formylpyridine-2-carbonitrileYield 57.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromonicotinaldehyde (11.2 g, 60 mmol) and CuCN (8.06 g, 90 mmol) in DMF (100 mL) was heated at 120° C. for 3 h under N2. The mixture was cooled to rt and diluted with EtOAc and filtered through a pad of celite. The organic layer was washed with water and brine and then dried (MgSO4) and concentrated. The product 5-formylpicolinonitrile (4.55 g) was obtained by silica gel chromatography (elution with 0-20% EtOAc/Hex).

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through a pad of celite
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d5c29c973f124377a0243a3300e00f2a
Source dataset
uspto-grants-2015_01
Patent number
US08940748B2

Reaction notes

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