Methyl iodide → 6-Chloro-4-methylamino-3-nitro-pyridine-2-carbonitrile
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12].[C:14](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.C(OCC)(=O)C>[CH3:14][NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A stirred mixture of 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (12.5 g), potassium carbonate (17.4 g) and iodomethane (22.5 g) in acetonitrile (150 ml) was heated at 80° C. for 3 hours. At this point, another portion of iodomethane (22.5 g) was added; the mixture was heated with stirring for another 2 hours. The mixture was then diluted with ethyl acetate (500 ml) and washed with water (150 ml). The organic layer was then dried over sodium sulphate, solvent removed under reduced pressure to give expected product 4-methylamino-6-chloro-3-nitro-pyridine-2-carbonitrile (13 g).
Workup
- temperaturethe mixture was heated
- washwashed with water (150 ml)
- dry with materialThe organic layer was then dried over sodium sulphate, solvent
- customremoved under reduced pressure
Sources & evidence
- ORD record
- ord-bae34a17d25042a18d2ed1826e0f858b
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026236B2
Reaction notes
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