Hydroxyamine hydrochloride → HCID 86744462, compound

HRID 1461434Notes

Reaction equation

HRID 1461434 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=O)[CH3:18].Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[N:21][OH:22])[CH3:18]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 150273831-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]ethanone

Product 1

HCID 86744462HCID 86744462, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-[2-[(2,6-Dichloro-3-methylphenyl)amino]phenyl]ethanone (0.8 g, 2.7 mmol) and hydroxylamine hydrochloride (0.8 g, 10.8 mmol) are dissolved in 15 ml of pyridine under argon at room temperature for 12 hours. The pyridine is evaporated, and the residue partitioned between methylene chloride and water. The organic layer is washed twice with 100 ml of water and dried over magnesium sulfate. The solution is concentrated on the rotovap and passed through a silica gel pad which is then eluted with methylene chloride. The solvent is evaporated and 1-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]ethanone oxime is recrystallized from H2O/MeOH. Yield 0.2 g (24%); mp 116°-118° C.

Workup

  1. customThe pyridine is evaporated
  2. customthe residue partitioned between methylene chloride and water
  3. washThe organic layer is washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution is concentrated on the rotovap
  6. washis then eluted with methylene chloride
  7. customThe solvent is evaporated
  8. custom1-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]ethanone oxime is recrystallized from H2O/MeOH

Sources & evidence

ORD record
ord-f9a7036b3f9a4d5a988f4dbbab8f1e22
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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