Iodine chloride → HCID 19867083, compound

HRID 568374Notes

Reaction equation

HRID 568374 reaction equation
[I:1]Cl.[CH3:3][C:4]1[CH:5]=[C:6]([N:15]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]2[CH3:21])[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH:10]=[CH:9]2.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:3][C:4]1[CH:5]=[C:6]([N:15]2[C:19]([I:1])=[C:18]([CH3:20])[N:17]=[C:16]2[CH3:21])[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 71305NanterinoneHCID 517045Sodium Acetate

Product 1

HCID 19867083HCID 19867083, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (0.406 g) was added at room temperature to a stirred solution of 8-methyl-6-(2,4-dimethylimidazol-1-yl)-2-(1H)-quinolone (0.506 g) and sodium acetate (0.328 g) in acetic acid (10 cm3). After 16 hours, volatile material was removed in vacuo and the residue partitioned between aqueous 2M sodium carbonate solution (50 cm3) and dichloromethane (50 cm3). The aqueous phase was further extracted with dichloromethane (2×50 cm3) and the combined and dried (MgSO4) organic extracts were filtered and evaporated in vacuo. The residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate. Combination and evaporation of the appropriate fractions afforded a solid which was recrystallised from ethyl acetatemethanol to give the title compound, m.p. 242°-245° (0.38 g).

Workup

  1. customvolatile material was removed in vacuo
  2. customthe residue partitioned between aqueous 2M sodium carbonate solution (50 cm3) and dichloromethane (50 cm3)
  3. extractionThe aqueous phase was further extracted with dichloromethane (2×50 cm3)
  4. dry with materialdried (MgSO4) organic extracts
  5. filtrationwere filtered
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  8. washeluting with ethyl acetate
  9. customCombination and evaporation of the appropriate fractions
  10. customafforded a solid which
  11. customwas recrystallised from ethyl acetatemethanol

Sources & evidence

ORD record
ord-4519820b9a82406788810ee48990c4b0
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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