Sodium Iodide → 6-Iodopyridine-3-carboxylic acid

HRID 1457353Notes

Reaction equation

HRID 1457353 reaction equation
[I-:1].[Na+].I.Cl[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1>CC(C)=O>[I:1][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 792226-Chloronicotinic acid

Product 1

HCID 8190626-Iodopyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 27.97 g (186.6 mmol) of sodium iodide cooled to -78° C. was added 121.77 g (71.6 ml, 952.0 mmol) of hydriodic acid (in 57 wt % aqueous solution). The reaction mixture was allowed to warm slightly with stirring for 5 minutes and then 30.00 g (190.4 mmol) of 6-chloronicotinic acid was added. The resulting mixture was allowed to warm to room temperature with stirring and then heated at 120°-125° C. in an oil bath for 42 hours. A dark brown layer formed above the yellow solid material. The reaction mixture was allowed to cool to room temperature and then poured into acetone (chilled to 0° C.). The resultant yellow solid was collected by filtration, washed with 200 ml of 1N aqueous NaHSO3 solution, and dried in vacuum (3 mm Hg) to give the title compound as a pale yellow solid. PMR (DMSO-d6): d 7.90 (1H, dd, J=8.1, 2 Hz), 7.99 (1H, d, J=8.1 Hz), 8.80 (1H, d, J=2 Hz).

Workup

  1. temperatureto warm slightly
  2. stirringwith stirring
  3. temperatureheated at 120°-125° C. in an oil bath for 42 hours
  4. customA dark brown layer formed above the yellow solid material
  5. temperatureto cool to room temperature
  6. filtrationThe resultant yellow solid was collected by filtration
  7. washwashed with 200 ml of 1N aqueous NaHSO3 solution
  8. customdried in vacuum (3 mm Hg)

Sources & evidence

ORD record
ord-fa0ec35e44764c4e90f0d902106df196
Source dataset
uspto-grants-1998_12
Patent number
US05847160

Reaction notes

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