Acetone → HCID 53955776, compound

HRID 1635517Notes

Reaction equation

HRID 1635517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5](OC)=O.[CH3:12][C:13]([CH3:15])=[O:14].[CH3:16][O-:17].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[CH2:5][C:16](=[O:17])[CH2:12][C:13](=[O:14])[CH3:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 53955776HCID 53955776, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of methyl 2-chloroisonicotinate (12.0 g, 0.07 mol) and acetone (12.2 g, 0.21 mol) in 100 mL of dry THF at 35 C was added sodium methoxide portionwise. After heating the reaction mixture at reflux for 4 h, the solvent was removed. The residue was dissolved with 500 mL of water, acidified with acetic acid to pH=6 and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give 11.46 g (83% yield) of product was a brown solid.

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureat reflux for 4 h
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved with 500 mL of water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c03ad49612a4b60891423e2efa4250a
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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