Ammonia → HCID 19867092, compound

HRID 649540Notes

Reaction equation

HRID 649540 reaction equation
I[C:2]1[N:3]=[C:4]([CH3:19])[N:5]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=2)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)[CH:6]=1.N.[CH3:21][N:22]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:21]([C:2]1[N:3]=[C:4]([CH3:19])[N:5]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=2)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)[CH:6]=1)#[N:22]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 14350348HCID 14350348, compound

Product 1

HCID 19867092HCID 19867092, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 6-(4-Iodo-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone (0.55 g), cuprous cyanide (0.27 g) and palladium acetate (0.03 g) in 1-methyl-2-pyrrolidone (5 cm3) was heated and stirred at 175° for 2 hours. The cooled mixture was poured into aqueous ammonia solution (30 cm3 ; S.G. 0.880) and extracted with dichloromethane (3×100 cm3). The combined and dried (MgSO4) organic extracts were filtered and evaporated in vacuo and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with chloroform. Combination and evaporation of the appropriate fractions afforded the title compound, m.p. >350°, (0.22 g).

Workup

  1. temperaturewas heated
  2. extractionextracted with dichloromethane (3×100 cm3)
  3. dry with materialdried (MgSO4) organic extracts
  4. filtrationwere filtered
  5. customevaporated in vacuo
  6. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  7. washeluting with chloroform
  8. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-f7d7aaff718540329124de1d66b2e2c5
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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