Hydrochloric Acid → 6-Chloro-2-iodo-3-hydroxypyridine

HRID 269584Notes

Reaction equation

HRID 269584 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I:15]I.Cl>O>[Cl:1][C:2]1[N:7]=[C:6]([I:15])[C:5]([OH:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 234331586-Chloro-2-iodo-3-hydroxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chloro-3-pyridinol (2.0 g, 15.44 mmol) was stirred in water (40 ml) containing sodium carbonate (3.43 g, 32.36 mmol) and iodine (3.92 g, 15.44 mmol) was added. The mixture was stirred at room temperature for 72 hours. The pH was adjusted to pH8 with 1M hydrochloric acid solution and the mixture extracted with ethyl acetate (×2). The combined organic extracts were washed with brine and dried (MgSO4). The aqueous layer was acidified to pH5 with 1M hydrochloric acid solution and extracted with ethyl acetate, which was washed with brine, dried (MgSO4) and the combined solutions evaporated to leave the title compound as a buff solid (3.70 g).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (×2)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. extractionextracted with ethyl acetate, which
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. customthe combined solutions evaporated

Sources & evidence

ORD record
ord-fda67ea3df394f178adaaec59d622444
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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