Sodium Iodide → 3-(3-Hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester

HRID 55262Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][N:7]=1.[I-:14].[Na+].Cl[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]([I:14])[N:7]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of 15 g of 3-(3-hydroxy-2-pyridyl)-propionic acid methyl ester in 250 ml of methanol is mixed with 12.4 g of sodium iodide, cooled to 15° C., and 74 ml of aqueous sodium hypochlorite solution (6.5% active chlorine) is instilled. The yellow suspension is concentrated by evaporation, the residue is taken up in water, acidified to pH 4 with 2n sulfuric acid and shaken out with ethyl acetate. The organic phase is washed with 10% sodium thiosulfate solution, dried with sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-50% ethyl acetate. 8.3 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester of melting point 145°-148° C. is obtained.

Workup

concentrationThe yellow suspension is concentrated by evaporation
washThe organic phase is washed with 10% sodium thiosulfate solution
dry with materialdried with sodium sulfate
concentrationconcentrated by evaporation
customthe residue is chromatographed on silica gel with hexane/0-50% ethyl acetate

Sources & evidence

ORD record: ord-5c60d194bd904e2d9f5dbe573c4587f2
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624943

Reaction notes

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