Hydroxyamine hydrochloride → Methyl 2-methoxy-5-formylbenzoate oxime

HRID 2230666Notes

Reaction equation

HRID 2230666 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=O.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:4]=1[C:5](=[N:16][OH:17])[O:7][CH3:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 10856352Methyl 5-formyl-2-methoxybenzoate

Product 1

HCID 86583897Methyl 2-methoxy-5-formylbenzoate oxime

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Combine methyl 2-methoxy-5-formylbenzoate (5.0 g, 25.9 mmol), hydroxylamine hydrochloride (8.55 g, 133 mmol), and sodium acetate (10.25 g, 125 mmol) in ethanol/water (200 mL, 1/1). Heat: to 50° C. After 1 hour, pour the reaction mixture onto ice to give a solid. Collect the solid byfiltration to give methyl 2-methoxy-5-formylbenzoate oxime: Rf=0.76 (silica gel, 9/1 dichloromethane/methanol).

Workup

  1. temperatureHeat
  2. customto 50° C
  3. additionpour the reaction mixture onto ice
  4. customto give a solid
  5. filtrationCollect the solid byfiltration

Sources & evidence

ORD record
ord-2536758a95db4b1db18b53321fd82247
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

Loading…