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

HRID 1393156Notes

Reaction equation

HRID 1393156 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 0.79 g (89%) of 4-(4-pyridyl)-2-butanone 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-a2454d7945f04bdf9d1b973d4698a4e9
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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