4-Methylpyridine → Dimethyl-(2-pyridin-4-yl-vinyl)-amine

HRID 2363935Notes

Reaction equation

HRID 2363935 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:8][N:9]([CH:11](N(C)C)OC(C)(C)C)[CH3:10]>CN(C=O)C>[CH3:8][N:9]([CH3:11])[CH:10]=[CH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 79634-MethylpyridineHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 391372Dimethyl-(2-pyridin-4-yl-vinyl)-amineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-methylpyridine (3.7 g, 40 mmol) and bis(dimethylamino)-tert-butoxymethane (8.44 g, 48 mmol) in DMF (10 mL) was heated at reflux for 12 hours under a nitrogen atmosphere and then concentrated under vacuum to give a tan solid. The product was re-crystallized from cyclohexane to give compound 4-(2-dimethylaminovinyl)pyridine (5.0 g, yield 85%) as light yellow crystals. A solution of 4-(2-dimethylaminovinyl)pyridine (5.0 g, 33.8 mmol), ethyl cyanoacetate (3.8 g, 33.8 mmol), sulfur (8.6 g, 270.2 mmol) and morpholine (1 mL) in EtOH (50 mL) was heated at 80° C. under a nitrogen atmosphere for 3 hours and chilled in ice. The resulting crystals were collected by filtration, washed with hexane, and dried to give the title compound (5.5 g, 66% yield) as an orange solid:

Workup

  1. temperatureat reflux for 12 hours under a nitrogen atmosphere
  2. concentrationconcentrated under vacuum
  3. customto give a tan solid
  4. customThe product was re-crystallized from cyclohexane

Sources & evidence

ORD record
ord-26b4add930e54cbc80cfa5d0569f2bae
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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