6-Chloropyridine-2-carbonitrile → HCID 13023645, compound

HRID 748198Notes

Reaction equation

HRID 748198 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1.[O-:10][CH2:11][CH3:12].[Na+]>O1CCCC1>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:10][CH2:11][CH3:12])[N:3]=1)#[N:9]

Participants

4

Reactant 2

HCID 1184246-Chloropyridine-2-carbonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 13023645HCID 13023645, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-chloro-6-cyanopyridine (1.00 g, 7.2 mmol), sodium ethoxide (0.54 g, 7.9 mmol) and tetrahydrofuran (100 ml) was refluxed for 18 hrs. The reaction mixture was concentrated under reduced pressure, diluted with ice-water and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (5:1, v/v) to give the titled compound (0.15 g, 14%).

Workup

  1. temperaturewas refluxed for 18 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with ice-water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. washeluted with hexane-ethyl acetate (5:1

Sources & evidence

ORD record
ord-5324c9bf455e49709cf2476db2457159
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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