Hydrochloric Acid → HCID 178491906, compound

HRID 620841Notes

Reaction equation

HRID 620841 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[C:13]1[NH:14][C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[C:16]([CH3:18])[N:17]=1.Cl.[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([NH2:10])=[CH:5][C:4]=1[C:13]1[NH:14][C:15]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[C:16]([CH3:18])[N:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178491908HCID 178491908, compound

Product 1

HCID 178491906HCID 178491906, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2-methoxy-4-chloro-5-nitrophenyl)-4-methyl-5-(3-pyridyl)imidazole (6.4 g), 1N-hydrochloric acid (37 ml) and 10% palladium on carbon (3 g) in methanol (100 ml) was subjected to catalytic reduction at ambient temperature under atmospheric pressure of hydrogen gas for 3 hours. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was dissolved in water and the solution was adjusted to pH 8.0 with 20% aqueous potassium carbonate. The resultant mixture was extracted with ethyl acetate and extract was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (96:4 V/V). The fractions containing object compound were evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 2-(2-methoxy-4-chloro-5-aminophenyl)-4-methyl-5-(3-pyridyl)imidazole (2.1 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionThe resultant mixture was extracted with ethyl acetate
  5. extractionextract
  6. dry with materialwas dried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. washeluted with a mixture of chloroform and methanol (96:4 V/V)
  9. additionThe fractions containing object compound
  10. customwere evaporated in vacuo
  11. customthe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-3dc1e263c9ff455e8b3bd04c4282c89f
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

Loading…