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

HRID 1959306Notes

Reaction equation

HRID 1959306 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-072e0500272345b5ae05537f1f4320be
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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