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

HRID 47061

Reaction equation

HRID 47061 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:14])[CH:12]=O>>[CH3:10][N:11]([CH3:14])[CH:12]=[CH:1][C:2]1[CH:3]=[CH:4][N:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 2278064-Methyl-3-cyanopyridine

Product 1

HCID 543988174-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrileYield 63%

Procedure

A solution of 4-methylnicotinonitrile (13.8 g, 0.12 m), dimethylformamide (DMF) (100 mL) and DMF acetal (14.0 g, 0.12 m) was heated at reflux under N2. After 16 hours, the reaction mixture was concentrated at atmospheric pressure until the internal temperature reached 150°. The mixture was then cooled, poured into H2O (1 L) and extracted with C6H6 (6×200 mL). The combined organic extracts were washed with H2O (2×200 mL), dried, filtered and evaporated to dryness. The residue was distilled at 150°-160° (0.2 mm) to yield 12.6 g (63%) of N,N-dimethyl-2-(3-cyano-4-pyridyl)ethenamine. An analytical sample was prepared by crystallization from C6H6 --C6H14, mp 88°-90°.

Workup

  1. temperatureat reflux under N2
  2. concentrationthe reaction mixture was concentrated at atmospheric pressure until the internal temperature
  3. customreached 150°
  4. temperatureThe mixture was then cooled
  5. additionpoured into H2O (1 L)
  6. extractionextracted with C6H6 (6×200 mL)
  7. washThe combined organic extracts were washed with H2O (2×200 mL)
  8. customdried
  9. filtrationfiltered
  10. customevaporated to dryness
  11. distillationThe residue was distilled at 150°-160° (0.2 mm)

Sources & evidence

ORD record
ord-6dbade8656ef4e5db9489c5be0401d9d
Source dataset
uspto-grants-1979_11
Patent number
US04176183

Linked notes

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