Water → Ethyl 6-hydroxy-5-iodonicotinate

HRID 1690193Notes

Reaction equation

HRID 1690193 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[I-:13].O>N1C=CC=CC=1>[OH:1][C:2]1[C:12]([I:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 30165Iodide IonHCID 178469094HCID 178469094, compound

Product 1

HCID 178469850Ethyl 6-hydroxy-5-iodonicotinateYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 6-hydroxynicotinate (2.0 g, 12.0 mmol) was dissolved in pyridine (60 mL), which was then added with iodide (6.07 g, 23.9 mmol) and stirred at 60° C. overnight. The reaction solution was then added with water at room temperature and extracted with ethyl acetate. Subsequently, the organic layer was washed with a saturated aqueous solution of sodium sulfite and brine, and dried over sodium sulfate. The obtained residue was purified using column chromatography (chloroform/methanol) and concentrated in vacuo. Ethyl 6-hydroxy-5-iodonicotinate (2.9 g, yield 83%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with a saturated aqueous solution of sodium sulfite and brine
  3. dry with materialdried over sodium sulfate
  4. customThe obtained residue was purified
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca1f2f17b944479d9b6fe4e4f2acb72e
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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