Iodine → 2-Chloro-3-iodopyridin-4-amine

HRID 536205Notes

Reaction equation

HRID 536205 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-:15].[K+].II.[OH-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Cl:1][C:2]1[C:7]([I:15])=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 6

HCID 807IodineHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 844322-Chloropyridin-4-amine

Product 1

HCID 242292082-Chloro-3-iodopyridin-4-amineYield 19.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Commercially available 2-chloro-4-aminopyridine (15 g, 0.1 mol) and 37.2 g (0.4 mol) of sodium carbonate are suspended in 200 ml of water and warmed to 100° C. 58.3 g (0.4 mol) of potassium iodide and 59.4 g (0.2 mol) of iodine are added to the resultant solution, and the mixture is stirred at the temperature indicated for 12 h. The mixture is subsequently adjusted to pH 13 using sodium hydroxide solution, treated with sodium thiosulfate until completely decolorised and extracted with ethyl acetate. Chromatographic purification gives 5 g (17%) of solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customChromatographic purification

Sources & evidence

ORD record
ord-a5e1bc3944384b66943ecd4470c3c552
Source dataset
uspto-grants-2014_10
Patent number
US08859581B2

Reaction notes

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