Sodium Bicarbonate → HCID 87871533, compound

HRID 856799Notes

Reaction equation

HRID 856799 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.[CH3:20][O:21][NH2:22].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:20][O:21]/[N:22]=[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)\[CH2:9][C:10]1[N:11]([CH2:15][CH2:16][CH3:17])[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22938877HCID 22938877, compound

Product 1

HCID 87871533HCID 87871533, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(4-aminophenyl)-2-(1-propylimidazol-2-yl)ethanone (600 mg) and O-methylhydroxylamine hydrochloride (227 mg) in ethanol (20 ml) was refluxed for 8 hours. 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 dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1), and washed with diisopropyl ether to give (1E)-1-(4-aminophenyl)-2-(1-propylimidazol-2-yl)ethanone O-methyloxime (230 mg) as colorless crystals.

Workup

  1. customto be at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=1:1)
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-c4ab84881d0f4857a468500b1709b3f2
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…