Sodium Iodide → 5-Chloro-6-iodo-3-nitropyridin-2-amine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([NH2:9])=[N:6][C:7]=1Cl.[I-:13].[Na+]>CC(O)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([NH2:9])=[N:6][C:7]=1[I:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 5,6-dichloro-3-nitropyridin-2-amine (15 g, 72.1 mmol) in AcOH (70 mL) was added sodium iodide (43.2 g 149.9 mmol). The mixture was stirred at 90° C. for 2 h, cooled to rt, diluted with water (70 mL) and filtered. The solid residue was washed with water, and then dried under vacuum to afford the desired product as a pale yellow solid, which was used in the next step without further purification. LC-MS: calculated for C5H3ClIN3O 2299.45, observed m/e: 299.94 (M+H)+ (Rt 2.18/5 min).
Workup
- temperaturecooled to rt
- filtrationfiltered
- washThe solid residue was washed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-324cce931dc44820a3fd7ae62763f44a
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796258B2
Reaction notes
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