O-Methylhydroxylamine hydrochloride → HCID 59916288, compound

HRID 635408Notes

Reaction equation

HRID 635408 reaction equation
Cl.[CH3:2][O:3][NH2:4].[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[C:13](=O)[C:14]([O:16][CH3:17])=[O:15]>CO>[CH3:2][O:3][N:4]=[C:13]([C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]=1[CH3:5])[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochloride2×HCID 18413297HCID 18413297, compound

Product 1

HCID 59916288HCID 59916288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

At room temperature (about 25° C.), 83.5 ml (0.15 mol) of a 15% strength solution of O-methylhydroxylamine hydrochloride in methanol were added dropwise to a mixture of 19.2 g (0.1 mol) of methyl 2,6-dimethylphenylglyoxylate and 100 ml of methanol. At the boiling point of the solvent, the resulting reaction mixture was stirred under reflux for 16 hours and then admixed with a further 24 ml of the 15% strength solution of O-methylhydroxylamine hydrochloride in methanol. After a further 32 h at the boiling point of the solvent, the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate. The organic phase was washed with water, dried and freed of the solvent under reduced pressure. The resulting residue (20 g) was purified by distillation. This gave 12 g of the title compound which can be subjected to the isomerization according to Example 3 without further purification.

Workup

  1. customAt the boiling point of the solvent, the resulting reaction mixture
  2. temperatureunder reflux for 16 hours
  3. customthe solvent was removed under reduced pressure
  4. washThe organic phase was washed with water
  5. customdried
  6. distillationThe resulting residue (20 g) was purified by distillation
  7. customaccording to Example 3 without further purification

Sources & evidence

ORD record
ord-a61f46436a514ab0beb34123bd3436eb
Source dataset
uspto-grants-2001_02
Patent number
US06187816B1

Reaction notes

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