Ammonium Hydroxide → 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+].[OH-].[NH4+]>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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-chloro-3-iodopyridin-2-amine (0.25 g, 0.982 mmol, Boa Pharma) in concd H2SO4 (1.95 mL) was cooled to about 0° C. before the portion wise addition of potassium nitrate (0.21 g, 2.2 mmol) over 10 min. The reaction was stirred for about 4 h at about 0° C. The reaction mixture was slowly pipetted over a solution of ammonium hydroxide and crushed ice (10 mL) in an ice bath. The pH of the reaction was maintained above 9 by the incremental addition of ammonium hydroxide. The resulting precipitate is filtered and dried to afford 4-chloro-3-iodo-5-nitropyridin-2-amine (0.085 g, 29%) as a green-tinted solid LC/MS (Table 1, Method n) Rt=0.64 min; MS m/z: 298 (M−H)−.
Workup
- filtrationThe resulting precipitate is filtered
- customdried
Sources & evidence
- ORD record
- ord-8500171c71b149e6810d2542a001a64d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426411B2
Reaction notes
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