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

HRID 1085472Notes

Reaction equation

HRID 1085472 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.C(O[CH:13](N(C)C)[N:14]([CH3:16])[CH3:15])(C)(C)C>CN(C)C=O>[CH3:13][N:14]([CH3:16])[CH:15]=[CH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][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 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 47 g 4-picoline and 105.5 g bis(dimethylamino)methyl tertiary-butyl ether in 125 ml dimethylformamide (DMF) was heated at 140° C. under nitrogen for 18 hours. The solvent was removed in vacuo and the crystalline residue dissolved in boiling cyclohexane (about 3 L). The solution was filtered through filter paper containing charcoal and concentrated in vacuo to give 60 g (80%) 4-(2-dimethylamino-1-ethenyl)pyridine as light orange crystals.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crystalline residue dissolved
  3. filtrationThe solution was filtered
  4. filtrationthrough filter paper
  5. additioncontaining charcoal
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f45cb7f2c7844e1986bea77b43c6dab
Source dataset
uspto-grants-1991_04
Patent number
US05010086

Reaction notes

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