Iodine chloride → 2-Chloro-5-iodopyridin-4-amine

HRID 384695Notes

Reaction equation

HRID 384695 reaction equation
[I:1]Cl.[Cl:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][N:5]=1.C([O-])(=O)C.[K+]>C(O)(=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([I:1])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 844322-Chloropyridin-4-amineHCID 517044Potassium Acetate

Product 1

HCID 454803662-Chloro-5-iodopyridin-4-amineYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (0.758 g, 4.67 mmol) was added to a solution of 2-chloro-4-amino pyridine (0.500 g, 3.89 mmol) and potassium acetate (0.763 g, 7.78 mmol) in acetic acid (30 mL). The reaction mixture was heated under reflux for 4 hr. The solvent was removed in vacuo and the residue was partitioned between aqueous sodium hydrogenocarbonate (50 mL) and ethyl acetate (50 mL). The organic phase was dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified by flash silica chromatography, eluting with ethyl acetate and hexane (1/9), to give the title compound as a pink solid (0.394 g, 40%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hr
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between aqueous sodium hydrogenocarbonate (50 mL) and ethyl acetate (50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified by flash silica chromatography
  8. washeluting with ethyl acetate and hexane (1/9)

Sources & evidence

ORD record
ord-19d502a4498c4ad4971a9645883bbac5
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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