Hydrochloric Acid → 4-(Pyridin-4-yl)butan-2-one

HRID 18394Notes

Reaction equation

HRID 18394 reaction equation
Cl.[C:2]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)C(OCC)=O)(=[O:4])[CH3:3]>>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:5][C:2](=[O:4])[CH3:3])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10680502Ethyl 2-(4-pyridylmethyl)acetoacetate

Product 1

HCID 127072234-(Pyridin-4-yl)butan-2-oneYield 110.1%

Procedure

Next, 6 N hydrochloric acid (8 ml) was added to ethyl 2-acetyl-3-(4-pyridyl)propionate (1.20 g, 4.81 mmol), and the mixture was refluxed for 1.5 hours. The reaction mixture was concentrated under reduced pressure, 2-propanol (10 ml) was added to the concentrate, and the whole was concentrated under reduced pressure again. Ethyl acetate was added to the resulting solid, and the solid was filtered off to give 4-(4-pyridyl)-2-butanone (0.79 g, 89%) as a pale yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, 2-propanol (10 ml)
  3. additionwas added to the concentrate
  4. concentrationthe whole was concentrated under reduced pressure again
  5. additionEthyl acetate was added to the resulting solid
  6. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-4541ff4cea6f4561ae2b219737f5c92f
Source dataset
uspto-grants-2010_06
Patent number
US07741346B2

Reaction notes

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