Sulfuric Acid → 4-Amino-2-hydroxybenzohydroxamic acid

HRID 1378639

반응식

HRID 1378639 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

HCID 4090774-Amino-2-hydroxybenzohydroxamic acid수율 89.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8638d5341dac4b5d9f39aab22249e20a
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668257

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