Cyanoacetamide → 5-Acetyl-2-hydroxy-6-methylnicotinonitrile
Reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8]OC(OC)N(C)C.[Na].[C:17]([CH2:19][C:20]([NH2:22])=[O:21])#[N:18]>C(O)C.C1COCC1>[C:5]([C:4]1[CH:8]=[C:19]([C:17]#[N:18])[C:20](=[O:21])[NH:22][C:1]=1[CH3:2])(=[O:7])[CH3:6]Participants
Procedure
A mixture of acetylacetone (41 ml), N,N-dimethylformamide dimethylacetal (106.2 ml) and THF (200 ml) was stirred at room temperature for 3 hours. After distilling off the solvent under reduced pressure, the residue was added dropwise to a solution prepared by dissolving metal sodium (13.8 g) in ethanol (600 ml) and adding thereto cyanoacetamide (33.6 g), and the mixture was refluxed for one hour. The reaction mixture was ice-cooled, and the precipitated crystals were separated by filtration. The crystals were dissolved in water (1 liter) and then weakly acidified with 3N hydrochloric acid. The precipitated crystals were separated by filtration and recrystallized from DMF-methanol to give 5-acetyl-6-methyl-1,2-dihydro-2-oxo-3-pyridinecarbonitrile (60 g) as colorless crystals. M.p. 230° C.
Workup
- distillationAfter distilling off the solvent under reduced pressure
- additionthe residue was added dropwise to a solution
- customprepared
- additionadding
- temperaturecooled
- customthe precipitated crystals were separated by filtration
- dissolutionThe crystals were dissolved in water (1 liter)
- customThe precipitated crystals were separated by filtration
- customrecrystallized from DMF-methanol
Sources & evidence
- ORD record
- ord-88ed1c488fdf480781764b394caa3fdc
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172079B2
Reaction notes
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