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

HRID 2278886Notes

Reaction equation

HRID 2278886 reaction equation
[OH:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I.Cl>O.CO>[I:15][C:5]1[N:4]=[C:3]([CH3:8])[C:2]([OH:1])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 707192-Methylpyridin-3-ol

Product 1

HCID 121942112-Methyl-3-hydroxy-6-iodopyridineYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-hydroxy-2-methylpyridine (20.0 g, 183 mmol) and Na2CO3 (38.8 g, 367 mmol) in H2O (320 mL) and MeOH (200 mL) was treated with I2 (46.5 g, 183 mmol) and stirred at RT for 1 h. The mixture was acidified with HCl (2 M), extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was suspended in 1:1 EtOAc/Hex, sonicated and the solid collected via filtration and dried. The filtrate was concentrated to dryness, treated with DCM, the solid collected via filtration and combined with the first solid to afford 6-iodo-2-methylpyridin-3-ol (20.5 g, 48%). MS (ESI) m/z: 236.0 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customsonicated
  6. filtrationthe solid collected via filtration
  7. customdried
  8. concentrationThe filtrate was concentrated to dryness
  9. additiontreated with DCM
  10. filtrationthe solid collected via filtration

Sources & evidence

ORD record
ord-c91538a3709646dda5901b26b1f731e5
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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