Hydroxyamine hydrochloride → 5-Carboxyethyl-2,4-dimethoxy-4'-methoxybenzophenone oxime

HRID 893419Notes

Reaction equation

HRID 893419 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=O)[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][C:4]=1[CH2:21][CH2:22][C:23]([OH:25])=[O:24].Cl.[NH2:27][OH:28].C([O-])(=O)C.[Na+]>C(O)C>[C:23]([CH2:22][CH2:21][C:4]1[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[C:6]([CH:5]=1)[C:11](=[N:27][OH:28])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 144609963-[2,4-Dimethoxy-5-(4-methoxybenzoyl)phenyl]propionic acid

Product 1

HCID 867459445-Carboxyethyl-2,4-dimethoxy-4'-methoxybenzophenone oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37 g of 3-[2,4-dimethoxy-5-(4-methoxybenzoyl)phenyl]propionic acid, 22.4 g of hydroxylamine hydrochloride and 21 g of sodium acetate (anhydrous) are added to 300 ml of absolute ethanol, and the mixture is refluxed with exclusion of moisture for 24 hours. Insolubles are removed by suction, the filtrate is concentrated, and water is added to the residue. The pH is then adjusted to 2 with 1N hydrochloric acid, and the mixture is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate and concentrated. The residue is recrystallized from ethyl acetate/hexane.

Workup

  1. temperaturethe mixture is refluxed with exclusion of moisture for 24 hours
  2. customInsolubles are removed by suction
  3. concentrationthe filtrate is concentrated
  4. additionwater is added to the residue
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0237181bebd849ebaf988bb108ec4ff4
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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