Hydrochloric Acid → HCID 58570265, compound

HRID 2278904Notes

Reaction equation

HRID 2278904 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:16]I.Cl>CO.O.[Cl-].[Na+].O.II>[I:16][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 150473662,4-Dimethyl-3-hydroxypyridine

Product 1

HCID 58570265HCID 58570265, compoundYield 84.1%

Reagents, catalysts & solvents 4

HCID 807IodineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2,4-dimethyl-3-hydroxypyridine (3.00 g, 24.36 mmol) and Na2CO3 (5.16 g, 48.7 mmol) in MeOH (40 mL) and water (24 mL) was treated with iodine (6.18 g, 24.36 mmol) and stirred at RT for 1 h. Additional iodine (0.4 g) was added, the mixture stirred at RT for 3 h, then acidified to pH=5 with 3M HCl. The mixture was treated with brine, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 6-iodo-2,4-dimethylpyridin-3-ol (5.1 g, 84%). MS (ESI) m/z: 250.0 (M+H+).

Workup

  1. stirringthe mixture stirred at RT for 3 h
  2. extractionextracted with EtOAc (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4d471e68686b4df9b537827d23d35e4f
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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