Hydrochloric Acid → 2-Chloro-3-hydroxy-6-iodopyridine

HRID 2075233Notes

Reaction equation

HRID 2075233 reaction equation
[I:1]I.[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>O>[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([I:1])[N:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 811362-Chloro-3-pyridinol

Product 1

HCID 107774172-Chloro-3-hydroxy-6-iodopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodine (2.38 mL, 46.3 mmol) was added to a solution of 2-chloro-3-pyridinol (5.00 g, 38.6 mmol) in water (60 mL) containing potassium carbonate (18.7 g, 135 mmol). The resulting solution was allowed to stir for 2 h at room temperature. The mixture was treated with sodium thiosulfate, acidified to pH 2 using 12M aqueous HCl, and extracted with EtOAc. The organic phase was dried over MgSO4 and evaporated. Purification by flash chromatography using EtOAc/hexanes gave 2-chloro-6-iodopyridin-3-ol. 1H NMR (300 MHz, CDCl3) δ ppm 7.56 (d, J=8.2 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H). MS (ESI) m/z: Calculated; 254.9 Observed: 255.8 (M++1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-68d0303ab9c349eab802a47a88b09b5e
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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