Iodine → 5-Iodo-3-methylpyridin-2-amine

HRID 2376040Notes

Reaction equation

HRID 2376040 reaction equation
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.O.O.[I:16](O)(=O)(=O)=O.II.[O-]S([O-])(=S)=O.[Na+].[Na+]>O.CC(O)=O>[I:16][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([NH2:8])=[N:4][CH:5]=1

Participants

8

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 153472-Amino-3-methylpyridineHCID 24477Sodium ThiosulfateHCID 86590690HCID 86590690, compound

Product 1

HCID 9595865-Iodo-3-methylpyridin-2-amineYield 207.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methyl-2-pyridinamine (10 g) in a mixed solution of AcOH (60 mL), water (12 mL), and sulfuric acid (4.2 mL) was added periodic acid dihydrate (4.22 g) and iodine (9.39 g), and the mixture was heated at 80° C. for 2 hours. The reaction mixture was poured into 5% Na2S2O3 aq solution and extracted with ether. The organic layer was washed with 1N NaOH aq solution and brine, and dried over Na2SO4. The solvent was removed in vacuo and obtained residual solid was recrystallized with EtOH to give 5-iodo-3-methyl-2-pyridinamine (9.00 g) as pale yellow powder.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with 1N NaOH aq solution and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customobtained residual solid
  6. customwas recrystallized with EtOH

Sources & evidence

ORD record
ord-f52906508b7a4878b00be5b6d9e2513e
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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