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

HRID 2208652Notes

Reaction equation

HRID 2208652 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>[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

5

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 47.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of t-BuOK (20.0 g, 179 mmol) and cyanoacetamide (16.5 g, 196 mmol) in DMSO (300 mL) was added (3E)-3-hepten-2-one (20.0 g, 178 mmol). The reaction mixture was stirred at 23° C. for 30 minutes and then additional t-BuOK (60.0 g, 712 mmol) was added to the reaction mixture. The reaction mixture was placed under oxygen atmosphere and stirred for 16 h. The reaction mixture was then purged with argon and was cooled to 0° C. The mixture was diluted with aq. HCl and the resulting precipitate was collected. The solid was washed with water and dried to give 6-methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile (15.0 g, 47% yield).

Workup

  1. stirringstirred for 16 h
  2. customThe reaction mixture was then purged with argon
  3. temperaturewas cooled to 0° C
  4. additionThe mixture was diluted with aq. HCl
  5. customthe resulting precipitate was collected
  6. washThe solid was washed with water
  7. customdried

Sources & evidence

ORD record
ord-d014099fba77438aa84fbe7e70a2b5e9
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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