Cyanoacetamide → 4-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[C:8]([CH3:11])([O-])[CH3:9].[K+].[CH3:13][C:14](=O)[C:15]#CC>CS(C)=O>[CH2:14]([C:15]1[CH:11]=[C:8]([CH3:9])[NH:6][C:4](=[O:5])[C:3]=1[C:1]#[N:2])[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-cyano-acetamide (841 mg, 10.0 mmol) in DMSO (20 mL) and potassium tert-butoxide (1.18 g, 10.5 mmol) was stirred at 23° C. for 30 minutes. The mixture was cooled to 0° C. then pent-3-yn-2-one (1.1 mL, 10 mmol) was added and the reaction mixture was stirred for 2 hours. The reaction mixture was quenched with saturated ammonium chloride (3 mL) then diluted with water (10 mL) causing a solid to precipitate out. The suspension was filtered and the solids dried under vacuum to give 4-ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cpd AA, 1.2 g, 71%) as a white solid.
Workup
- customThe reaction mixture was quenched with saturated ammonium chloride (3 mL)
- additionthen diluted with water (10 mL)
- customto precipitate out
- filtrationThe suspension was filtered
- customthe solids dried under vacuum
Sources & evidence
- ORD record
- ord-14bdf5d6d4774de886a89dcb49ff59b6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040515B2
Reaction notes
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