Acetone → HCID 18676105, compound

HRID 1635509Notes

Reaction equation

HRID 1635509 reaction equation
CO[C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([Cl:10])[CH:5]=1.[CH3:12][C:13]([CH3:15])=[O:14].C[O-].[Na+]>C1COCC1>[Cl:10][C:6]1[CH:5]=[C:4]([C:3](=[O:11])[CH2:12][C:13](=[O:14])[CH3:15])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 18676105HCID 18676105, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl-2-chloroisonicotinate (11.93 g, 69.53 mmol) in THF (200 mL) was added acetone (14.19 mL, 153 mmol). The solution was warmed to 35° C. when sodium methoxide (94.13 g, 76.48 mmol) was added sequentially over 20 minutes. The mixture was stirred for 30 minutes, and then brought to reflux for 2.5 hours. The solvent was removed under reduced pressure and then taken up in ethyl acetate. The resulting solution was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated to yield 1-(2-chloro-4-pyridinyl)-1,3-butanedione (4.97 g, 76%) as a light brown colored solid. This was used in the next step without further purification.

Workup

  1. additionwas added sequentially over 20 minutes
  2. temperatureto reflux for 2.5 hours
  3. customThe solvent was removed under reduced pressure
  4. washThe resulting solution was washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2a4a2ed81b55422b97bfaa273fd74a31
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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