Ammonia → HCID 19867079, compound

HRID 568376Notes

Reaction equation

HRID 568376 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17](I)=[C:16]([CH3:19])[N:15]=[C:14]2[CH3:20])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.N.ClCCl.[CH3:25][N:26]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[C:17]([C:25]#[N:26])=[C:16]([CH3:19])[N:15]=[C:14]2[CH3:20])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 13387N-methyl-2-pyrrolidoneHCID 19867083HCID 19867083, compound

Product 1

HCID 19867079HCID 19867079, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 8-methyl-6-(2,4-dimethyl-5-iodoimidazol-1-yl)-2-(1H)-quinolone (0.1 g), cuprous cyanide (0.047 g) and palladium acetate (0.01 g), in N-methyl-2-pyrrolidone (1 cm3) was heated and stirred at 175° for 3 hours. The cooled mixture was poured into aqueous ammonia solution (10 cm3 ; S.G. 0.880) and dichloromethane (50 cm3) and the aqueous phase was further extracted with dichloromethane (2×50 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 dichloromethane:methanol, 19:1. Combination and evaporation of appropriate fractions afforded an oil which crystallised on trituration with ether to give the title compound, m.p. 334°-337° (0.03 g).

Workup

  1. extractionthe aqueous phase was further extracted with dichloromethane (2×50 cm3)
  2. dry with materialdried (MgSO4) organic extracts
  3. filtrationwere filtered
  4. customevaporated in vacuo
  5. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washeluting with dichloromethane
  7. customCombination and evaporation of appropriate fractions
  8. customafforded an oil which
  9. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-69e0d6c835004fd5b8a002ffbcea75f7
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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