Hydroxyamine hydrochloride → 5-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23822Notes

Reaction equation

HRID 23822 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH2:10][CH:11]=O)=[O:8].Cl.[NH2:16][OH:17].[C:18]([O-:21])(=O)C.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH2:10][CH2:11][N:16]([CH:18]=[O:21])[OH:17])=[O:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 225906095-bromo-2-chloro-N-(2-oxo-ethyl)-benzamide

Product 1

HCID 225906105-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-chloro-N-(2-oxo-ethyl)-benzamide (11.8 g, 42.5 mmol) in MeOH (400 mL) was added hydroxylamine hydrochloride (5.9 g, 85 mmol) and sodium acetate (6.97 g, 85 mmol). The mixture was stirred 18 h and the MeOH was removed in vacuo. The residue was washed with water and was dried in vacuo for 18 h and used without further purification to provide the title compound (11.7 g, 94%) as a white solid. ESMS: M+H=291.

Workup

  1. customthe MeOH was removed in vacuo
  2. washThe residue was washed with water
  3. customwas dried in vacuo for 18 h
  4. customused without further purification

Sources & evidence

ORD record
ord-3a55e9682d6b4d388a4708eee96a9a63
Source dataset
uspto-grants-2005_02
Patent number
US06852882B2

Reaction notes

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