Hydrochloric Acid → 4-Chloro-1-(pyridin-3-YL)butan-1-one

HRID 727803Notes

Reaction equation

HRID 727803 reaction equation
[C:1]([O:9]C)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:11]1[CH2:16]OC(=O)[CH2:12]1.C[O-].[Na+].[ClH:20].C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:20][CH2:12][CH2:11][CH2:16][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7151Methyl NicotinateHCID 7302Gamma-ButyrolactoneHCID 516892Sodium BicarbonateHCID 10942334Sodium Methoxide

Product 1

HCID 124710054-Chloro-1-(pyridin-3-YL)butan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl nicotinate (59 g, 0.43 mol), 4-hydroxybutyric acid lactone (51.8 g, 0.602 mol), and sodium methoxide (70 g, 1.29 mol) in dioxane (500 mL) is refluxed for 1 hour and then cooled. Concentrated hydrochloric acid (650 mL) is added, and the reaction mixture is refluxed for 12 hours. The resulting solution is neutralized with solid sodium bicarbonate and extracted with chloroform. The organic phase is dried (sodium sulfate), and the solvent evaporated in vacuo. The residue is taken up in 2-propanol (50 mL) and treated with a saturated solution of hydrogen chloride in 2-propanol. The hydrochloride salt of 4-chloro-1-(3-pyridinyl)-1-butanone is obtained as a white solid (30 g); mp 73°-76° C.

Workup

  1. temperaturecooled
  2. temperaturethe reaction mixture is refluxed for 12 hours
  3. extractionextracted with chloroform
  4. dry with materialThe organic phase is dried (sodium sulfate)
  5. customthe solvent evaporated in vacuo
  6. additiontreated with a saturated solution of hydrogen chloride in 2-propanol

Sources & evidence

ORD record
ord-b818a0d5d8884ee6a72ef7ea35aed322
Source dataset
uspto-grants-1991_09
Patent number
US05045550

Reaction notes

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