Potassium Nitrate → 4-chloro-3-iodo-5-nitropyridin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9].[N+:10]([O-])([O-:12])=[O:11].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[I:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-chloro-3-iodopyridin-2-amine (4.00 g, 15.7 mmol, Adesis) in concd H2SO4 (45 mL) was cooled to about 0° C. in an ice bath. Potassium nitrate (3.50 g, 34.6 mmol) was added in four portions over about 10 min. The resulting solution was stirred at about 0° C. for about 1 h, then at ambient temperature for about 4 h. The reaction mixture was slowly poured over crushed ice (total volume 1 L) resulting in formation of a solid that was collected by vacuum filtration and dried under vacuum to give 4-chloro-3-iodo-5-nitropyridin-2-amine (2.2 g, 47%) as a yellow solid: LC/MS (Table 1, Method c) Rt=1.48 min; MS m/z 298 (M−H)−.
Workup
- waitat ambient temperature for about 4 h
- additionThe reaction mixture was slowly poured
- customover crushed ice (total volume 1 L)
- customresulting in formation of a solid
- filtrationthat was collected by vacuum filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-34211e888e8c4ac6bd8353791b8f8d4c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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