Hydroxyamine hydrochloride → HCID 87871529, compound

HRID 856800Notes

Reaction equation

HRID 856800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]2[N:11]([CH2:15][CH2:16][CH3:17])[CH:12]=[CH:13][N:14]=2)=[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](/[C:8](=[N:20]/[OH:21])/[CH2:9][C:10]2[N:11]([CH2:15][CH2:16][CH3:17])[CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22938877HCID 22938877, compound

Product 1

HCID 87871529HCID 87871529, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-aminophenyl)-2-(1-propylimidazol-2-yl)ethanone (600 mg) and hydroxylamine hydrochloride (223 mg) in ethanol (20 ml) was refluxed for 1 day. After the mixture was allowed to be at room temperature, and saturated sodium bicarbonate solution was added to the mixture, the mixture was extracted with ethyl acetate and washed with water and saturated brine. The mixture was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was washed with ethyl acetate-diisopropyl ether to give (1E)-1-(4-aminophenyl)-2-(1-propylimidazol-2-yl)ethanone oxime (419 mg) as yellow crystals.

Workup

  1. customto be at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-c3cb251fb2064bf2957989aaf828c5e2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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