Hydrochloric Acid → 2-Chloro-4-[2-(hydroxyimino)acetamido]benzoic acid

HRID 1822896Notes

Reaction equation

HRID 1822896 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[C:18]([Cl:25])[CH:17]=1.Cl.Cl.[NH2:28][OH:29]>O>[Cl:25][C:18]1[CH:17]=[C:16]([NH:15][C:3](=[O:5])[CH:2]=[N:28][OH:29])[CH:24]=[CH:23][C:19]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 171544-Amino-2-chlorobenzoic acidHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 714168982-Chloro-4-[2-(hydroxyimino)acetamido]benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of chloral hydrate (1.0 g, 6.00 mmol; Spectrum Quality Products, Inc., New Brunswick, N.J.) and water (80 mL) was added sodium sulfate (5 g), 4-amino-2-chloro-benzoic acid (855 mg, 4.98 mmol; Acros), concentrated aq. HCl (5 mL) and hydroxylamine hydrochloride (1.15 g, 16.5 mmol; Aldrich). It was refluxed for 20 minutes. The mixture was cooled to rt, the precipitate was filtered and washed with water. The title compound (1.08 g, 90%) was obtained as a white solid.

Workup

  1. temperatureIt was refluxed for 20 minutes
  2. filtrationthe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-84e81932c6c44fe2bcd47b015cd8ccfe
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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