Dimethylformamide → 3-[2-(Dimethylamino)ethenyl]pyridine-2-carbonitrile
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]=1Participants
3
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
- customThe solution was then evaporated to dryness
- customto give a crude oil which
- customThe solid was crystallized from ligroin
Sources & evidence
- ORD record
- ord-9b7b082db0304f9b872f64baf33f2cfb
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04176183
Reaction notes
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