Iodine → 2-Iodo-6-methylpyridin-3-ol

HRID 416559

Reaction equation

HRID 416559 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[N:12][CH:13]=1.[I:15]I.[I-].[K+]>O>[I:15][C:13]1[C:8]([OH:7])=[CH:9][CH:10]=[C:11]([CH3:14])[N:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 899572-Iodo-6-methylpyridin-3-olYield 43.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium carbonate (68.0 g) and water (810 mL) were added to 5-hydroxy-2-methylpyridine (1-014-01) (36.11 g), and the reaction mixture was stirred at room temperature, dissolved. To the reaction mixture was added dropwise a solution of iodine (117 g) and potassium iodide (117 g) in water (810 mL) for 35 min. The resulting pink-yellow crystal was filtered and dried under reduced pressure to give 2-iodo-3-hydroxy-6-methylpyridine (2-014-01) (34.1 g, 43.9%, m.p. 187-190° C.)

Workup

  1. dissolutiondissolved
  2. filtrationThe resulting pink-yellow crystal was filtered
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-a2e97d959c4e4dd8b6b848baa7230577
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Linked notes

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