Hydrochloric Acid → Ethanone, 1-(4-aminophenyl)-, O-methyloxime

HRID 450050Notes

Reaction equation

HRID 450050 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=O.Cl.[CH3:12][O:13][NH2:14].Cl>C(O)C>[CH3:12][O:13][N:14]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7468p-AminoacetophenoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 87589734Ethanone, 1-(4-aminophenyl)-, O-methyloximeYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-amino acetophenone (650 mg, 4.8 mmol) and O-methyl-hydroxylamine hydrochloride (800 mg, 9.6 mmol) in ethanol (10 ml) was added a drop of conc. hydrochloric acid and the reaction was heated to reflux for 2 hr. The solvent was evaporated under reduced pressure and ethyl acetate was added, washed with water, dried over anhydrous sodium sulphate, and then filtered. Evaporation yielded 1-(4-aminophenyl)-ethanone-O-methyl-oxime (700 mg, 89%) as a solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hr
  3. customThe solvent was evaporated under reduced pressure and ethyl acetate
  4. additionwas added
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customEvaporation

Sources & evidence

ORD record
ord-0f28cb535c084bd4946934aa91c31b6e
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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