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

HRID 2092543Notes

Reaction equation

HRID 2092543 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 sulfate (25 g) were added. To this reaction mixture, conc. HCl (7.5 mL) was slowly added. The reaction mixture was stirred at 90° C. for 3 h. The precipitate was formed and was collected by filtration. The solid was dried to get 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); LC-MS (ESI): Calculated mass: 260.0; Observed mass: 259.0 [M−H]+ (RT: 0.88 min).

Workup

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

Sources & evidence

ORD record
ord-fba10ba2b4b540919a52d1ccc26fe75e
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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