Acetone → 1-(2-Cyanoisonicotinyl)-1,3-butanedione

HRID 1635501

Reaction equation

HRID 1635501 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6](OC)=O)#[N:2].[CH3:13][C:14]([CH3:16])=[O:15].[CH3:17][O-:18].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[CH2:6][C:17](=[O:18])[CH2:13][C:14](=[O:15])[CH3:16])#[N:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 10942334Sodium MethoxideHCID 12132796Methyl 2-cyanopyridine-4-carboxylate

Product 1

HCID 544384121-(2-Cyanoisonicotinyl)-1,3-butanedioneYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of methyl 2-cyanoisonicotinate (20.0 g, 0.126 mol) in 250 mL THF was added acetone (30.6 mL, 0.42 mol). The solution was warmed to 35° C. and sodium methoxide (7.15 g, 0.132 mol) was added portionwise over 20 minutes. The mixture was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue was dissolved in water, acidified to pH=6 with acetic acid. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 13.0 g (58% yield) of product as a brown solid, which was used in next step without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in water
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-605ada101eb74710a60f749723efbd6f
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Linked notes

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