Hydrochloric Acid → (2E)-N-(4-bromo-3-methoxyphenyl)-2-hydroxyiminoacetamide

HRID 245147Notes

Reaction equation

HRID 245147 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].Cl.Cl[C:13](Cl)(Cl)[CH:14]([OH:16])O.[O-]S([O-])(=O)=O.[Na+].[Na+].[NH2:26][OH:27].Cl>O.O1CCOCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:16])/[CH:13]=[N:26]/[OH:27])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 70182544-Bromo-3-methoxyaniline

Product 1

HCID 14595057(2E)-N-(4-bromo-3-methoxyphenyl)-2-hydroxyiminoacetamideYield 111.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-3-(methyloxy)aniline (50 g, 247 mmol), HCl (100 mL) and dioxane (150 mL) in H2O (500 mL) was stirred at 50° C. 2,2,2-Trichloro-1,1-ethanediol (81.7 g, 494 mmol), Na2SO4 (526 g, 3705 mmol) and H2O (1 L) were added to the mixture followed by NH2OH.HCl (103 g, 1482 mmol in 100 mL of H2O). The mixture was stirred at 80° C. for 1 h, cooled to room temperature, filtered and washed with H2O to yield (2E)-N-[4-bromo-3-(methyloxy)phenyl]-2-(hydroxyimino)ethanamide (75 g) as a yellow solid. MS (m/z) 273 (M+H+).

Workup

  1. stirringThe mixture was stirred at 80° C. for 1 h
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washwashed with H2O

Sources & evidence

ORD record
ord-cd35bce504984b59999165bdf887ceac
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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