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

HRID 226355

Reaction equation

HRID 226355 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.[I:14](O)(=O)(=O)=O.II.[O-]S([O-])(=S)=O.[Na+].[Na+]>O.CC(O)=O>[I:14][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 65185Metaperiodic acid

Product 1

HCID 9595865-Iodo-3-methylpyridin-2-amineYield 174.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methyl-2-pyridineamine (10 g) in a mixed solution of AcOH (60 mL), water (12 mL), and sulfuric acid (4.2 mL) was added periodic acid dehydrate (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-53f55ca96c1d4c3cab9aef891b414de3
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Linked notes

Loading…