Sulfuric Acid → 4-Amino-2-hydroxybenzohydroxamic acid

HRID 234169

Reaction equation

HRID 234169 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[O-]S([O-])=O.[Na+].[Na+].[NH2:12][C:13]1[CH:14]=[C:15]([OH:23])[C:16](=[CH:21][CH:22]=1)[C:17](OC)=[O:18].OS(O)(=O)=O>O>[NH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH:4][OH:1])=[O:18])=[C:15]([OH:23])[CH:14]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 77787Methyl p-aminosalicylateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 4090774-Amino-2-hydroxybenzohydroxamic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaOH (4.0 grams) in 16 mL of water is carefully added to hydroxylamine hydrochloride (2.8 grams, 40 mmol) and 20 grams of ice. After dissolution, Na2SO3 (0.4 grams) is added, followed by methyl 4-aminosalicylate (3.35 grams, 20 mmol). The resulting solution is stirred for up to 24 hours at room temperature, the course of the reaction is monitored every few hours by reverse phase HPLC. The resulting solution is chilled on ice and acidified by addition of 25% H2SO4. A precipitate is first formed at approx. pH 6. The pH is finally adjusted to approx. pH 4, and the pale tan precipitate collected by filtration. The product is dried in vacuo over P2O5, to afford 3.0 grams (89% yield) of 4-amino-2-hydroxybenzohydroxamic acid (m.p. 180°-181° C). The structure was confirmed by 1H NMP, spectrometry in d6 -DMSO.

Workup

  1. additionis added
  2. waitthe course of the reaction is monitored every few hours by reverse phase HPLC
  3. temperatureThe resulting solution is chilled on ice
  4. customA precipitate is first formed at approx. pH 6
  5. filtrationthe pale tan precipitate collected by filtration
  6. dry with materialThe product is dried in vacuo over P2O5

Sources & evidence

ORD record
ord-bedb80c473874b34a94da0cebd1beb71
Source dataset
uspto-grants-1997_01
Patent number
US05594151

Linked notes

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