O-Methylhydroxylamine hydrochloride → HCID 136127060, compound

HRID 432054Notes

Reaction equation

HRID 432054 reaction equation
O1C2C=CC=CC=2C(=O)C1=NO.Cl.CON.[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1/[C:24](=[N:29]\[O:30][CH3:31])/[C:25]([O:27][CH3:28])=[O:26].OC1C=CC=CC=1/C(=N/OC)/C(OC)=O>CO>[OH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[N:29][O:30][CH3:31])[C:25]([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 135424589methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetateHCID 135703866HCID 135703866, compoundHCID 178516824HCID 178516824, compound

Product 1

HCID 136127060HCID 136127060, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.2 g (0.05 mol) of benzofuran-2,3-dione 2-oxime and 9 g (0.108 mol) of O-methylhydroxylamine hydrochloride in 50 ml of methanol are heated under reflux for 3 hours. The methanol is distilled off under reduced pressure and the residue is mixed with 50 ml of water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure, giving 9.88 g of crystal-containing crude product. According to HPLC, the crude product contains 43.7% of methyl E-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=1.48 and 29.4% of methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.37.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationThe methanol is distilled off under reduced pressure
  3. additionthe residue is mixed with 50 ml of water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customgiving 9.88 g
  8. additionof crystal-containing crude product

Sources & evidence

ORD record
ord-4315cc39b10b4d7ea0f723b6ad7ee611
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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