Isopropyl iodide → HCID 22493581, compound

HRID 1263469Notes

Reaction equation

HRID 1263469 reaction equation
[Cl:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12](=O)([O-])[O-].[K+].[K+].I[CH:19]([CH3:21])[CH3:20].C([O:25][CH2:26][CH3:27])(=O)C.CCCCCC>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[N:4][CH2:5][C:6]([O:25][CH:26]([CH3:27])[CH3:12])([C:7]([O:9][CH:19]([CH3:21])[CH3:20])=[O:8])[CH:10]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 178524771HCID 178524771, compound

Product 1

HCID 22493581HCID 22493581, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 20 ml of N,N-dimethylformamide were dissolved 1.0 g of 5-chloro-6-hydroxynicotinic acid. To the resulting solution were added 4.78 g of potassium carbonate and 1.26 ml of 2-iodopropane, followed by stirring under heat at 80° C. for 4 hours. Ice water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and, concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 5% ethyl acetate/n-hexane), whereby 600 mg of the title compound were obtained.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue so obtained

Sources & evidence

ORD record
ord-588f910140c946a2843e92929e4f7490
Source dataset
uspto-grants-2003_04
Patent number
US06541474B2

Reaction notes

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