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

HRID 1725849Notes

Reaction equation

HRID 1725849 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-60f9fa94bab04b739f548d9484005fea
Source dataset
uspto-grants-2009_02
Patent number
US07491739B2

Reaction notes

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