Methylamine → 2-(Methylamino)pyridine-3-carbonitrile
Reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][NH2:11]>>[CH3:10][NH:11][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Participants
3
Procedure
A solution of 2-chloronicotinonitrile (97.82 g, 706 mmol) in 40% aqueous methylamine (706 ml) was heated to reflux for 1.5 hour. The excess methylamine was evaporated off and the resulting solids filtered and washed with water (250 mL). The crude product was dissolved in boiling water (1.4 1) and treated with charcoal and filtered through Celite. The aqueous filtrate was cooled to room temperature. After 10 hours the crystalline solid was collected, washed with water and dried to leave 71.10 g of 2-(methylamino)-nicotinonitrile (mp. 86-88 degrees C.). A sample was further purified by sublimation (100 degrees C. at 0.025 mm) mp. (87-88 degrees C.).
Workup
- temperatureto reflux for 1.5 hour
- customThe excess methylamine was evaporated off
- filtrationthe resulting solids filtered
- washwashed with water (250 mL)
- dissolutionThe crude product was dissolved
- additiontreated with charcoal
- filtrationfiltered through Celite
- customAfter 10 hours the crystalline solid was collected
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-8f3bc1710cbd4d06aaf3bdf45d6d7c6e
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05002944
Reaction notes
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