Water → HCID 86071606, compound

HRID 2263551Notes

Reaction equation

HRID 2263551 reaction equation
[OH-].[Na+].I[C:4]1[C:9]([OH:10])=[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:7]=[C:6]([I:17])[N:5]=1.[CH3:18]I.O>CN(C)C=O.C(OCC)(=O)C>[I:17][C:6]1[CH:7]=[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]([O:10][CH3:18])=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 23149482HCID 23149482, compound

Product 1

HCID 86071606HCID 86071606, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 60 mmol NaOH in 50 ml N,N-dimethyl formamide is progressively added 50 mmol 2,6-diiodo-4-(4-methoxy-butyl)-pyridin-3-ol. The reaction mixture is stirred for 30 minutes and then cooled to 0° C. 60 mmol methyl iodide are added and the mixture is stirred for 15 minutes at room temperature. Water and ethyl acetate are added to the mixture, the layers are separated and the aqueous layer is extracted with ethyl acetate (3×). The combined organic layers are dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60 F) and identified based on its Rf value.

Workup

  1. stirringthe mixture is stirred for 15 minutes at room temperature
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layers are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9e61a3f015f24ec4b09636b88de9df82
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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