Ethanol → 1-Hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole

HRID 620820Notes

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.C(O)C.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=O.O.[NH3:29]>O1CCOCC1.O>[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:29]=[C:21]1[C:20]1[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 1-hydroxyimino-1-(3-pyridyl)acetone (1.64 g) in a mixture of dioxane (30 ml), ethanol (10 ml), and water (5 ml) were added 3,4-dimethoxybenzaldehyde (1.66 g) and conc. ammonia water (0.69 ml). The solution was stirred at 60° C. for 2 hours. Additional ammonia water (0.7 ml) was added thereto, and the solution was stirred at 45° to 50° C. for 1 day. The mixture was evaporated, and the residue was dissolved in chloroform, and subjected to column chromatography on silicagel eluting with a mixture of chloroform and methanol. The fractions were collected and evaporated, and the residue was triturated with diisopropyl ether to give 1-hydroxy-2-(3,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.20 g).

Workup

stirringthe solution was stirred at 45° to 50° C. for 1 day
customThe mixture was evaporated
dissolutionthe residue was dissolved in chloroform
washon silicagel eluting with a mixture of chloroform and methanol
customThe fractions were collected
customevaporated
customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-ecd1190dd0804c37a318d8da51e6cd8f
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822805

Reaction notes

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