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

HRID 637203Notes

Reaction equation

HRID 637203 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

Conditions

Temperature
50 °C

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 by filtration to give methyl 2-methoxy-5-formylbenzoate oxime: Rf=0.76 (silica gel, 9/1 dichloromethane/methanol).

Workup

  1. additionpour the reaction mixture onto ice
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration

Sources & evidence

ORD record
ord-adeef8c50f5d404ea4f4c0abeffe5041
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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