Cyanoacetamide → 5-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1032995

Reaction equation

HRID 1032995 reaction equation
[CH2:1]([CH:3]([C:6](=O)[CH3:7])[CH2:4]O)[CH3:2].[Na].[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].C([O-])(=O)C.[NH2+]1CCCCC1>O.C(O)(=O)C>[C:10]([C:12]1[C:13](=[O:14])[NH:15][C:1]([CH3:2])=[C:3]([CH2:6][CH3:7])[CH:4]=1)#[N:11]

Participants

7

Reactant 4

HCID 7898CyanoacetamideHCID 2702992-Ethyl-3-oxobutanolHCID 3014295Piperidinium acetateHCID 5360545Sodium

Product 1

HCID 102411095-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Accordingly to the method described in J. Heterocyclic Chem., 24, 351 (1987), a mixture 2-ethyl-3-oxobutanol, sodium salt (37.5 g, 0.275 mol), cyanoacetamide (25.2 g, 0.30 mol), aqueous piperidinium acetate (22 mL) [prepared from glacial acetic acid (4.2 mL), water (10 mL) and piperidine (7.2 mL)] in water (775 ml) was refluxed for four hours. Glacial acetic acid (30 ml) was added cautiously (much foaming) as the product precipitated. Upon cooling to room temperature, the product was collected by filtration, washed with cold water and air dried to yield 22.3 g (50%), m.p. 237°-240° C.

Workup

  1. customprecipitated
  2. filtrationthe product was collected by filtration
  3. washwashed with cold water and air
  4. customdried
  5. customto yield 22.3 g (50%), m.p. 237°-240° C.

Sources & evidence

ORD record
ord-c602bf6ca4ee4f1e85995269cf1af67f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Linked notes

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