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

HRID 751440Notes

Reaction equation

HRID 751440 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-7619f2c18af94b63856d800d916e05c8
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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