Potassium Iodide → HCID 16073871, compound

HRID 1068000Notes

Reaction equation

HRID 1068000 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:36][CH2:37][O:38][CH2:39][CH2:40][OH:41]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:36][CH2:37][O:38][CH2:39][CH2:40][OH:41])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 178522861HCID 178522861, compound

Product 1

HCID 16073871HCID 16073871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide (0.37 gm) from Preparation No. 5 in DMF (10 mL) is treated with potassium carbonate (2.75 gm), potassium iodide (1.66 gm) and 2-(2-chloroethoxy)ethanol (1.0 mL). The mixture is tightly capped and heated to 100° C. for 48 hrs. The reaction mixture is allowed to cool to room temperature, poured into water and extracted with dichloromethane. The layers are separated and the aqueous layer is re-extracted with dichloromethane containing a small amount of methanol and finally again with dichloromethane. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 3% to 15% methanol in dichloromethane and then by recrystallization from methanol to afford 82 mg of the title compound as a light yellow solid.

Workup

  1. customThe mixture is tightly capped
  2. temperatureto cool to room temperature
  3. extractionextracted with dichloromethane
  4. customThe layers are separated
  5. extractionthe aqueous layer is re-extracted with dichloromethane containing a small amount of methanol
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by flash column chromatography
  10. washeluting with 3% to 15% methanol in dichloromethane
  11. customby recrystallization from methanol

Sources & evidence

ORD record
ord-c00f8f600269441bbf533e4c320b8b08
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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