Iodine → 6-Acetyl-2-chloro-3-hydroxy-4-iodo-pyridine

HRID 1637784Notes

Reaction equation

HRID 1637784 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH:9]([OH:11])[CH3:10])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[I:18]I>O>[C:9]([C:4]1[N:3]=[C:2]([Cl:1])[C:7]([OH:8])=[C:6]([I:18])[CH:5]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 807IodineHCID 11430Potassium CarbonateHCID 106073192-Chloro-6-(1-hydroxyethyl)pyridin-3-ol

Product 1

HCID 187995586-Acetyl-2-chloro-3-hydroxy-4-iodo-pyridineYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-3-hydroxy-6-(1-hydroxyethyl)pyridine (7.19 g, 41.4 mmole) was dissolved in 80 ml of water containing potassium carbonate (17.2 g, 124 mmole) in a 200 ml one neck round bottom flask. The solution was treated with iodine (31.5 g, 124 mmole) and was stirred for 6 h at room temperature. The mixture was quenched with saturated sodium thiosulfate and the pH was adjusted to 2 with 12 N hydrochloric acid. The precipitate was collected, was washed with water, and was dried. The yellow solid was further washed with diethyl ether to provide 4.68 g (38%) of 6-acetyl-2-chloro-3-hydroxy-4-iodo-pyridine as a pale tan solid (Melting Point: 223-224° C.).

Workup

  1. customThe mixture was quenched with saturated sodium thiosulfate
  2. customThe precipitate was collected
  3. washwas washed with water
  4. customwas dried
  5. washThe yellow solid was further washed with diethyl ether

Sources & evidence

ORD record
ord-cca06b3cbe44485ab41416bb2b764df4
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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