Cyanoacetamide → 6-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile

HRID 1616496Notes

Reaction equation

HRID 1616496 reaction equation
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][C:14](=O)/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH3:19]>CS(C)=O.O.Cl>[CH3:13][C:14]1[NH:12][C:10](=[O:11])[C:9]([C:7]#[N:8])=[C:16]([CH2:17][CH2:18][CH3:19])[CH:15]=1

Participants

7

Reactant 3

HCID 7898CyanoacetamideHCID 53645783-Hepten-2-oneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 156418016-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrileYield 33%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of t-BuOK (1 g, 8.9 mmol) in DMSO (15 mL) at rt, was added compound cyanoacetamide (0.824 g, 9.8 mmol) and (E)-hept-3-en-2-one (1 g, 8.91 mmol). Reaction mixture was stirred for 30 min at rt. Additional t-BuOK (3 g, 26.7 mmol) was added and reaction was stirred at rt in presence of air. On completion, it was diluted with H2O and slowly by 4N HCl. Precipitated solid was filtered, washed with water and dried. Crude product was triturated with ether to afford the title compound (0.5 g, 33%).

Workup

  1. customReaction mixture
  2. customreaction
  3. stirringwas stirred at rt in presence of air
  4. customPrecipitated solid
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried
  8. customCrude product was triturated with ether

Sources & evidence

ORD record
ord-25f2984e005543078222512144cd4207
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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