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

HRID 1820952Notes

Reaction equation

HRID 1820952 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I:15]I.Cl>O.CO>[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:15])[N:3]=1

Participants

7

Reactant 4

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

Product 1

HCID 121942112-Methyl-3-hydroxy-6-iodopyridineYield 46%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1.05 g (9.62 mmol) of 2-methyl-3-hydroxypyridine and 2.04 g (19.24 mmol) of sodium carbonate in 10 mL of H2O and 5 mL of CH3OH was added 2.44 g (9.62 mmol) of iodine in several portions. After stirring at rt for 30 min, the reaction mixture was acidified using 5.0 N HCl until pH=3. The mixture was extracted with EtOAc (3×20 mL). Organic layers were combined, dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded 1.04 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 2.28 (s, 3H), 6.76 (d, J=8.2, 1H), 7.34 (d, J=8.7, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01af0a90f6164796b62bda5fb9f88f08
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…