Ammonia → HCID 20141776, compound

HRID 649547Notes

Reaction equation

HRID 649547 reaction equation
[Cl:1][C:2]1[N:6]([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)[C:5]([CH3:19])=[N:4][C:3]=1I.N.[CH3:22][N:23]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:6]([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)[C:5]([CH3:19])=[N:4][C:3]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 20141778HCID 20141778, compound

Product 1

HCID 20141776HCID 20141776, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 6-(5-chloro-4-iodo-2-methylimidazol-1-yl)-8-methyl-2-(1H)quinolone (1.0 g), cuprous cyanide (0.45 g) and palladium acetate (0.09 g) in 1-methyl-2-pyrrolidone (5 cm3) was stirred and heated at 160° for 4 hours. The cooled mixture was poured into aqueous ammonia solution (30 cm3 ; S.G. 0.880) and extracted with ethyl acetate (3×150 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 methanol:dichloromethane, 1:200 by volume. Combination and evaporation of the appropriate fractions afforded the title compound as a solid (0.54 g) which was characterised spectroscopically and used directly without further purification.

Workup

  1. temperatureheated at 160° for 4 hours
  2. extractionextracted with ethyl acetate (3×150 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 methanol
  8. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-ad79aa0f1c8043c3848377a5213a15ef
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

Loading…