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

HRID 2379674Notes

Reaction equation

HRID 2379674 reaction equation
[CH2:1]([CH:3]([C:6](=O)[CH3:7])[CH: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 3014295Piperidinium acetateHCID 5360545SodiumHCID 152284102-Ethyl-3-oxobutanal

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

According to the method described in J. Heterocyclic Chem., 24, 351 (1987), a mixture of 2-ethyl-3-oxobutanal, sodium salt (37.5 g, 0.275 mmol), 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. temperaturewas refluxed for four hours
  2. customprecipitated
  3. filtrationthe product was collected by filtration
  4. washwashed with cold water and air
  5. customdried
  6. customto yield 22.3 g (50%), m.p. 237°-240° C.

Sources & evidence

ORD record
ord-3eb125fc7c6d4e7ca7f0df2afa760b15
Source dataset
uspto-grants-1994_11
Patent number
US05364776

Reaction notes

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