Cyanoacetamide → Ethyl 5-cyano-1,6-dihydro-2-methyl-6-oxo-3-pyridinecarboxylate
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=O)[CH3:2].C[O:11][CH:12](OC)[N:13](C)C.[C:18]([CH2:20][C:21](N)=O)#[N:19].[H-].[Na+]>C1COCC1.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:21]=[C:20]([C:18]#[N:19])[C:12](=[O:11])[NH:13][C:6]=1[CH3:8])=[O:9])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Ethylacetoacetate (6.5 g, 0.050 mole) and dimethylformamide dimethyl acetal (7.14 g, 0.060 mole) were stirred together under argon overnight. The resulting reddish oil was concentrated on the rotary evaporator and the concentrate then dissolved in THF (10 ml) and quickly added to a suspension of cyanoacetamide (4.20 g, 0.050 mole) and sodium hydride in THF (175 ml). The reaction mixture was heated and stirred overnight at 50° C. The reaction mixture was neutralized to pH 6 with acetic acid and concentrated on the rotary evaporator. The residue was triturated with a 50:50 CH2Cl2 -H2O mixture collected and recrystallized (EtOAC) giving 4.7 g of 3-cyano-1,2-dihydro-6-methyl-2-oxo-5-pyridinecarboxylic acid ethyl ester m.pt. 208°-210° C.
Workup
- concentrationThe resulting reddish oil was concentrated on the rotary evaporator
- concentrationthe concentrate
- dissolutionthen dissolved in THF (10 ml)
- temperatureThe reaction mixture was heated
- concentrationconcentrated on the rotary evaporator
- customThe residue was triturated with a 50:50 CH2Cl2 -H2O mixture
- customcollected
- customrecrystallized (EtOAC)
Sources & evidence
- ORD record
- ord-b559f2e8e49844a48c5394f9b5bd3134
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04853395
Reaction notes
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