Iodine → (5-Iodo-pyridin-2-yl)-methyl-amine

HRID 2109181

Reaction equation

HRID 2109181 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[I:9]I.C([O-])(O)=O.[Na+]>CC(O)=O.O>[I:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 807IodineHCID 207272-Pyridinamine, N-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 11253290(5-Iodo-pyridin-2-yl)-methyl-amineYield 24.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methylaminopyridine (Aldrich; 1.00 g, 9.25 mmol) in 10 mL of 1:1 HOAc and water was added 2.35 g (9.25 mmol) of I2. The resulting brown solution was heated to 80° C. for 3 h. After cooling to room temperature, the mixture was neutralized with saturated NaHCO3 and extracted with Et2O. The extract was washed with water and brine, dried with MgSO4, filtered, and concentrated to provide 540 mg of (5-iodo-pyridin-2-yl)-methyl-amine.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with Et2O
  3. washThe extract was washed with water and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ad8aeb0ab5848fbbff8dd26fcbe6a44
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Linked notes

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