Potassium Iodide → HCID 13560729, compound

HRID 414838Notes

Reaction equation

HRID 414838 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:14](=[O:17])([O-])[O-].[K+].[K+].[I-].[K+].[C:22](=[O:25])([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:22]([C:7]1[CH:6]=[C:14]([CH:10]=[CH:9][CH:8]=1)[O:17][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)(=[O:25])[CH2:11][CH2:12][CH2:13][CH2:4][CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 13560729HCID 13560729, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This ketone (1.2 g) was refluxed with 2-chloromethylquinoline hydrochloride (1.3 g), potassium carbonate (8.6 g), potassium iodide (0.05 g) and cesium carbonate (0.05 g) in acetone (300 ml) for 24 hours. The reaction mixture was filtered, and the filtrate was concentrated, dissolved in chloroform, and then washed with sodium hydroxide solution (5%), water and brine. After drying this solution over MgSO4, all volatiles were removed. The residue was purified by chromatography on silica gel (25% ethyl acetate in hexanes). The pure desired product was isolated as a tan solid, m.p. 52°-55° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutiondissolved in chloroform
  4. washwashed with sodium hydroxide solution (5%), water and brine
  5. dry with materialAfter drying this solution over MgSO4
  6. customall volatiles were removed
  7. customThe residue was purified by chromatography on silica gel (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-676dbe56a74944e5aa184ea58b8ab008
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

Loading…