Iodine → HCID 86639427, compound

HRID 1690208Notes

Reaction equation

HRID 1690208 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH2:2][CH3:3].[I:11]I>C(O)C.O>[I:11][C:6]1[N:5]=[C:4]([CH2:1][CH2:2][CH3:3])[C:9]([OH:10])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 2339742-propylpyridin-3-ol

Product 1

HCID 86639427HCID 86639427, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

2-Propylpyridin-3-ol (2.42 g, 17.7 mmol) was dissolved in ethanol (40 mL) and water (10 mL). Iodine (4.71 g, 18.6 mmol) was added thereto under ice-cold conditions, and stirred for 2 hours. Then, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, ethanol was concentrated in vacuo and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane/ethyl acetate), and 6-iodo-2-propylpyridin-3-ol (2.80 g, yield 60%) was obtained as a yellow oil.

Workup

  1. stirringThen, the mixture was stirred at room temperature for 4 hours
  2. concentrationwas concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-b4bc600f88fc4346a6f552b2388f42eb
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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