Hydroxyamine hydrochloride → (1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime

HRID 856804Notes

Reaction equation

HRID 856804 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[C:9](/[C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=[N:20]\[OH:21])=[CH:4][CH:3]=1.[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[C:9](/[C:11]2[N:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][N:15]=2)=[N:20]/[OH:21])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 229387292-(4-Aminophenyl)-1-(1-propylimidazol-2-yl)ethanone

Product 2

HCID 135829454(1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oximeHCID 136334097(1E)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone (400 mg) and hydroxylamine hydrochloride (149 mg) in ethanol (15 ml) was refluxed for 1 day. The mixture was allowed to be at room temperature, saturated sodium bicarbonate solution was added to the mixture, extracted with ethyl acetate, and washed with saturated brine. The mixture was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate) and recrystallized from hexane-ethyl acetate, to give (1E)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime (220 mg) and (1Z)-2-(4-aminophenyl)-1-(1-propylimidazol-2-yl)ethanone oxime (58 mg) as pale red crystals.

Workup

  1. customto be at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate)
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c1921629dd274c1c82099d045871b295
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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