2-Methoxy-4-methylbenzaldehyde → 1-Hydroxy-2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole

HRID 620822Notes

Reaction equation

HRID 620822 reaction equation
[OH:1][N:2]=[C:3]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[C:4]([CH3:6])=O.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.O.[NH3:25]>O1CCOCC1.C(O)C>[OH:1][N:2]1[C:3]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:4]([CH3:6])[N:25]=[C:17]1[C:16]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:15]=1[O:14][CH3:13]

Participants

6

Reactant 3

HCID 64237932-Methoxy-4-methylbenzaldehydeHCID 12896473Azane;hydrateHCID 737518861-Hydroxyimino-1-(3-pyridyl)acetone

Product 1

HCID 100858711-Hydroxy-2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1-hydroxyimino-1-(3-pyridyl)acetone (1.0 g) in a mixture of dioxane (20 ml) and ethanol (6 ml), were added 2-methoxy-4-methylbenzaldehyde (1.01 g) and conc. ammonia water (15 ml). The solution was stirred at ambient temperature for 8 days. After evaporation, the residue was dissolved in chloroform, and chromatographed on silicagel eluting with a mixture of chloroform and methanol. The fractions were collected, evaporated, and triturated in diisopropyl ether to give 1-hydroxy-2-(2-methoxy-4-methylphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.46 g).

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in chloroform
  3. customchromatographed
  4. washon silicagel eluting with a mixture of chloroform and methanol
  5. customThe fractions were collected
  6. customevaporated
  7. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-d78419dfb36044f8a11c657a73a94922
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

Loading…