4-Aminosalicylic Acid → 4-Acetamidosalicylic acid

HRID 1681583

Reaktionsgleichung

Reaktionsgleichung von HRID 1681583
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)C>[C:12]([NH:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7])(=[O:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 46494-Aminosalicylic AcidHCID 7918Acetic Anhydride

Produkt 1

HCID 655094-Acetamidosalicylic acidAusbeute 74.088,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred, refluxing suspension of 4-aminosalicylic acid (76.57 g, 0.5 mmol) in 250 mL absolute ethanol was added dropwise, over a 30 minute period, acetic anhydride (83.2 g, 0.815 mmol). After the addition was complete, the mixture was refluxed for another 15 minutes and then cooled. The product collected by filtration, washed with small amount of ethanol and dried on air to give 72.3 g (74.15%) of the title compound as a grey solid mp 242°14 4° C. Previously reported mp: 234°-5° C. (P. Barraclough et al. Eur. J. Chem. 25, p 467, 1990).

Aufarbeitung

  1. temperatureTo a stirred, refluxing
  2. additionwas added dropwise, over a 30 minute period
  3. additionAfter the addition
  4. temperaturethe mixture was refluxed for another 15 minutes
  5. temperaturecooled
  6. filtrationThe product collected by filtration
  7. washwashed with small amount of ethanol
  8. customdried on air

Quellen und Nachweise

ORD-Eintrag
ord-6720a5e7d7eb4460826c07c0c33658fc
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05173486

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