Acetic Acid → 1-Ethyl-3-cyano-5,6-dimethyl-2-pyridone
Reaction equation
[Na].[CH3:2][CH:3]([C:6](=O)[CH3:7])[CH:4]=O.[CH2:9]([NH:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH3:10].C(O)(=O)C.N1CCCCC1>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:9]([N:11]1[C:6]([CH3:7])=[C:3]([CH3:4])[CH:2]=[C:13]([C:14]#[N:15])[C:12]1=[O:16])[CH3:10]Participants
7
Conditions
- Temperature
- 135 °C
Procedure
To a suspension of 2-methyl-3-oxobutanal sodium salt (3.18 g) and N-ethylcyanoacetamide (3-0003-02) (2.243 g) in DMF (20 mL) were added acetic acid (1.49 mL) and piperidine (0.40 mL) at room temperature, and the reaction mixture was refluxed with stirring in an oil bath at 135° C. for 5 h. The reaction mixture was dissolved in chloroform and water, extracted three times with chloroform, dried over magnesium sulfate, and evaporated under reduced pressure. The obtained crystal residue (4.07 g) was washed three times with n-hexane (1 mL) to give 1-ethyl-3-cyano-5,6-dimethyl-2-pyridone (3-003-03) (3.38 g, 96%) as a brown crystal.
Workup
- temperaturethe reaction mixture was refluxed
- extractionwater, extracted three times with chloroform
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- washThe obtained crystal residue (4.07 g) was washed three times with n-hexane (1 mL)
Sources & evidence
- ORD record
- ord-2fa80b6da10a4e92ae41425fc35c60f0
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088924B2
Reaction notes
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