Hydrochloric Acid → N-(3-bromo-4-fluoro-phenyl)-2-hydroxyimino-acetamide

HRID 2284394Notes

Reaction equation

HRID 2284394 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].Cl[C:11](Cl)(Cl)[CH:12]([OH:14])O.Cl.[NH2:18][OH:19].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:14])[CH:11]=[N:18][OH:19])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 27792863-Bromo-4-fluoroaniline

Product 1

HCID 86665761N-(3-bromo-4-fluoro-phenyl)-2-hydroxyimino-acetamideYield 61.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 500 mL round bottom flask, 3-bromo-4-fluoraniline (5 g, 0.0261 mol), water (300 mL), chloral hydrate (5.19 g, 0.0314 mol), hydroxylamine hydrochloride (5.8 g, 0.0835 mol) and sodium sulphate (25 g) were added. To this reaction mixture, concentrated HCl (7.5 mL) was slowly added. The reaction mixture was stirred at 90° C. for 3 hours. A precipitate formed and was collected by filtration. The solid was dried to provide the title compound (4.2 g, 61%). 1H NMR (300 MHz, DMSO-d6): δ 12.28 (s, 1H), 10.51 (s, 1H), 8.12 (dd, J=2.4 Hz, J=2.7 Hz, 1H), 7.68 (m, 2H), 7.36 (t, J=8.7 Hz, 1H).

Workup

  1. customA precipitate formed
  2. filtrationwas collected by filtration
  3. customThe solid was dried

Sources & evidence

ORD record
ord-09a5ad5751bf4eb8818ec28b798c3f4c
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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