Potassium Carbonate → 2-(2-Fluorophenyl)-1-hydroxy-4-methyl-5-(3-pyridyl)imidazole

HRID 620839Notes

Reaction equation

HRID 620839 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.[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.C([O-])(=O)C.[NH4+:26].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]1[N:2]([OH:1])[C:3]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:4]([CH3:6])[N:26]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 517165Ammonium AcetateHCID 737518861-Hydroxyimino-1-(3-pyridyl)acetone

Product 1

HCID 103332812-(2-Fluorophenyl)-1-hydroxy-4-methyl-5-(3-pyridyl)imidazoleYield 28%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution 1-hydroxyimino-1-(3-pyridyl)acetone (0.5 g) in acetic acid (10 ml) was added 2-fluorobenzaldehyde (0.76 g) and ammonium acetate (2.35 g), and refluxed for 30 minutes. Then, the solution was poured into water (75 ml), neutrallized with aqueous potassium carbonate, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated, and the residue was triturated with diisopropyl ether to give 2-(2-fluorophenyl)-1-hydroxy-4-methyl-5-(3-pyridyl)imidazole (0.23 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-70513545ded44daea38c5ae6eea9060e
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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