2-Methoxybenzaldehyde → 1-Hydroxy-2-(2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

HRID 620819Notes

Reaction equation

HRID 620819 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.O.[NH3:14].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O>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:14]=[C:19]1[C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[O:16][CH3:15]

Participants

6

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 12896473Azane;hydrateHCID 737518861-Hydroxyimino-1-(3-pyridyl)acetone

Product 1

HCID 99938631-Hydroxy-2-(2-methoxyphenyl)-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 (1.5 g) in a mixture of dioxane (30 ml) and ethanol (8 ml) were added conc. ammonia water (40 ml) and 2-methoxybenzaldehyde (1.24 g), and the mixture was stirred at ambient temperature for 8 days. After evaporation, the mixture was triturated with chloroform to give 1-hydroxy-2-(2-methoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.65 g).

Workup

  1. customAfter evaporation
  2. customthe mixture was triturated with chloroform

Sources & evidence

ORD record
ord-10cd22c819554387bf9189122c2377db
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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