Dimethylformamide dimethyl acetal → 4-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrile

HRID 1723016Notes

Reaction equation

HRID 1723016 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[CH3:9])#[N:2].CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CN(C=O)C>[CH3:12][N:13]([CH3:15])[CH:14]=[CH:9][C:8]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2278064-Methyl-3-cyanopyridine

Product 1

HCID 543988174-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-cyano-4-methylpyridine (25 g, 0.21 mol), and N,N-dimethylformamide dimethyl acetal (29.2 mL, 0.22 mol) in dry DMF was heated at reflux overnight. Most of the DMF was removed under reduced pressure. The crude red oil was partitioned between EtOAc (300 mL) and H2O (300 mL) and the organic phase was washed with H2O, brine and dried (Na2SO4). Removal of the solvent afforded the product (34.3 g, 94%, as a light red solid of suitable purity for use directly in the next step, mp 80°-83° C.). An analytical sample was prepared by recrystallizing a sample of the crude product from benzene/petroleum ether, (mp 88°-89° C., light red solid).

Workup

  1. temperatureat reflux overnight
  2. customMost of the DMF was removed under reduced pressure
  3. customThe crude red oil was partitioned between EtOAc (300 mL) and H2O (300 mL)
  4. washthe organic phase was washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent
  7. customafforded the product (34.3 g, 94%
  8. customAn analytical sample was prepared
  9. customby recrystallizing a sample of the crude product from benzene/petroleum ether, (mp 88°-89° C., light red solid)

Sources & evidence

ORD record
ord-e3231572211b40de9e20731f4604de98
Source dataset
uspto-grants-1989_08
Patent number
US04859671

Reaction notes

Loading…