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

HRID 1897799Notes

Reaction equation

HRID 1897799 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].[I:14]Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([I:14])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 844322-Chloropyridin-4-amineHCID 517045Sodium Acetate

Product 1

HCID 454803662-Chloro-5-iodopyridin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A 100 mL round bottom flask was charged with 2-chloro-4-amino pyridine (3.0 g, 23.34 mmol), sodium acetate (11.49 g, 140 mmol) and acetic acid (60 mL). To this iodine monochloride (3.98 g, 24.50 mmol) was added and the reaction mixture stirred at 60° C. for 2 h. The reaction was cooled to room temperature and quenched with 1N saturated sodium bis-sulfite solution and extracted with DCM. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gel flash chromatography using DCM-MeOH:95-5. 2-Chloro-5-iodo-pyridin-4-ylamine was obtained as a white color solid. ESI-MS: m/z 255.0 (M+H)+

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with 1N saturated sodium bis-sulfite solution
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5258220304ad43eeb0772ffe624d7da0
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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