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

HRID 516717Notes

Reaction equation

HRID 516717 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 32%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of DMSO (300 mL) containing t-BuOK (20 g, 178 mmol) and cyanoacetamide (16.5 g, 196 mmol) was added (3E)-3-hepten-2-one (20 g, 178 mmol), and the contents were stirred at room temperature for 30 min. Additional t-BuOK (60 g, 534 mmol) was added and the reaction mixture was placed under an atmosphere of oxygen for an additional 1 h. The reaction mixture was purged with argon, diluted with 4 volumes of H2O, and then 5 volumes of 4 N HCl, which were added slowly. The reaction mixture was filtered, washed with water, and dried to give 6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinecarbonitrile (10 g, 32%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.25-12.40 (br s, 1H), 6.18 (s, 1H), 2.53 (t, 2H), 2.22 (s, 3H), 1.57-1.64 (m, 2H), 0.84 (t, 3H).

Workup

  1. waitthe reaction mixture was placed under an atmosphere of oxygen for an additional 1 h
  2. customThe reaction mixture was purged with argon
  3. additiondiluted with 4 volumes of H2O
  4. addition5 volumes of 4 N HCl, which were added slowly
  5. filtrationThe reaction mixture was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-6b6d7a59e80b4b249efd7aa687d0bf3e
Source dataset
uspto-grants-2015_08
Patent number
US09114141B2

Reaction notes

Loading…