Potassium Hydroxide → 5-Chloro-2-[2-(6-chloro-2-pyridyl)propen-3-yl]-2-methylindan 1,3-dion

HRID 1461633Notes

Reaction equation

HRID 1461633 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH3:14])[C:7]2=[O:15].[Cl:16][C:17]1[N:22]=[C:21]([C:23]([CH2:25]Cl)=[CH2:24])[CH:20]=[CH:19][CH:18]=1>CO.[I-].[K+]>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH2:25][C:23]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[N:22]=1)=[CH2:24])([CH3:14])[C:7]2=[O:15]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 150087112-Chloro-6-(3-chloroprop-1-en-2-yl)pyridineHCID 539304495-Chloro-2-methylindan-1,3-dione

Product 1

HCID 151168185-Chloro-2-[2-(6-chloro-2-pyridyl)propen-3-yl]-2-methylindan 1,3-dionYield 87%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 1.32 g of 85% potassium hydroxide, and then 3.89 g of 5-chloro-2-methylindan-1,3-dione, 3.76 g of 6-chloro-2-(1-chloromethylvinyl)pyridine and 0.05 g of potassium iodide were added to the solution. After refluxing under heating for 3 hours, the solvent was evaporated and water was poured. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water and with a saturated saline solution, and then dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was separated and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=5/1) to obtain 6.02 g of the compound No. 115 shown in Table 1.

Workup

  1. temperatureAfter refluxing
  2. temperatureunder heating for 3 hours
  3. customthe solvent was evaporated
  4. additionwater was poured
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with water and with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the solvent was evaporated
  9. customthe residue was separated
  10. custompurified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ede28d899e7843c5873d4f5d0c3499ea
Source dataset
uspto-grants-1991_12
Patent number
US05076830

Reaction notes

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