Hydroxyamine hydrochloride → 1-(3,4-Dichlorophenyl)-2-phenyl-ethan-1-one oxime

HRID 343088Notes

Reaction equation

HRID 343088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>O.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[N:19][OH:20])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27581451-(3,4-Dichlorophenyl)-2-phenylethanone

Product 1

HCID 867535841-(3,4-Dichlorophenyl)-2-phenyl-ethan-1-one oximeYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)-2-phenyl-ethan-1-one (Step 1) (12.5 g, 53.88 mmol), hydroxylamine hydrochloride (9.4 g, 135.4 mmol) and sodium acetate (268.5 mmol) in ethanol water (1:1, 250 mL) was heated at reflux for 4 hours, then was diluted with water (200 mL). The precipitate formed was filtered, dried and was recrystallized from hexane to afford 10 g (75%) of the desired product: mp 81°-82° C. 1H NMR (CDCl3) 7.50-7.06 (m, 9H), 4.18 (s, 2H). Found: Anal. Calc'd for C14H11NOCl2 :

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. customdried
  6. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-504fdd9302394fc5bae8277793aa5222
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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