Iodine → 6-Chloro-2-iodopyridin-3-amine

HRID 1713422Notes

Reaction equation

HRID 1713422 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[I:9]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:8][C:5]1[N:6]=[C:7]([I:9])[C:2]([NH2:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 807IodineHCID 793055-Amino-2-chloropyridine

Product 1

HCID 184070436-Chloro-2-iodopyridin-3-amine

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

5-Amino-2-chloropyridine (5.0 g, 0.039 mol) was dissolved in EtOH (25 mL), and silver sulfate (13.3 g, 0.043 mol) and iodine (10.9 g, 0.043 mol) were added. The reaction was stirred at room temperature overnight, and then the mixture was filtered over Celite to remove solids. The filtrate was concentrated and purified on silica gel (0-50% EtOAc in hexanes) to give the desired product.

Workup

  1. filtrationthe mixture was filtered over Celite
  2. customto remove solids
  3. concentrationThe filtrate was concentrated
  4. custompurified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4842d397b4674db190adee20fd43a4dd
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

Loading…