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

HRID 47063

Reaction equation

HRID 47063 reaction equation
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][N:11]([CH:13]=O)[CH3:12]>>[CH3:10][N:11]([CH3:13])[CH:12]=[CH:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 537133073-[2-(Dimethylamino)ethenyl]pyridine-2-carbonitrileYield 56%

Procedure

A solution of 3-methyl-2-cyanopyridine (20.0 g, 0.17 m), DMF (200 mL) and DMF acetal (30 mL, 0.25 m) was heated at 120° with stirring under N2 for 5 days. Additional acetal was periodically added in 5 mL aliquots (total 45 mL, 0.38 m). The solution was then evaporated to dryness to give a crude oil which solidified on standing. The solid was crystallized from ligroin to yield 16.5 g (56%) of N,N-dimethyl-2-(2-cyano-3-pyridyl)ethenamine. An analytical sample was prepared by recrystallization from ligroin, mp 71.5°-72°.

Workup

  1. customThe solution was then evaporated to dryness
  2. customto give a crude oil which
  3. customThe solid was crystallized from ligroin

Sources & evidence

ORD record
ord-9b7b082db0304f9b872f64baf33f2cfb
Source dataset
uspto-grants-1979_11
Patent number
US04176183

Linked notes

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