Hydroxyamine hydrochloride → HCID 85177110, compound

HRID 1451094Notes

Reaction equation

HRID 1451094 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH:15]=O)(=[O:3])[CH3:2].Cl.[NH2:18][OH:19]>C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[CH:15]=[N:18][OH:19])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 12464019HCID 12464019, compound

Product 1

HCID 85177110HCID 85177110, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-acetylamino-3-formylbenzoate (Gassman, P. G.; Drews, H. R. J. Am. Chem. Soc. 1978, 100, 7600-7610) (0.442 g, 0.002 mol) and hydroxylamine hydrochloride (0.174 g, 0.0025 mol) in ethyl acetate (10 mL) was heated at reflux for 16 h. White precipitate formed which was removed by filtration and the filtrate was concentrated to dryness. The residue was recrystallized from ethyl acetate-hexane to give 0.25 g (53%) of methyl 4-acetylamino-3-[(N-hydroxylimino)methyl]benzoate as a pale yellow powder, mp 200°-203° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customWhite precipitate formed which
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0e765bfd74ed45f29bc9e6a2c809baaf
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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