Sulfuric Acid → Methyl 5-amino-2-hydroxybenzoate

HRID 66223

Reaktionsgleichung

Reaktionsgleichung von HRID 66223
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:17][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([NH2:1])[CH:10]=1)[OH:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 40755-Aminosalicylic AcidHCID 10340Sodium Carbonate

Produkt 1

HCID 135127Methyl 5-amino-2-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 20.0 g of 5-aminosalicylic acid, 250 ml of methanol and 10 ml of concentrated sulfuric acid is refluxed overnight. The reaction mixture is cooled, made alkaline with dilute aqueous sodium carbonate solution and concentrated. The resulting solid is separated and washed with water. The solid is then washed with ether, and the ether is evaporated to dryness yielding a brown solid. The aqueous filtrate above is extracted with ether, the extract is dried over anhydrous sodium sulfate, and evaporated yielding a brown solid. The solids are combined and recrystallized from ether to afford 10.7 g of 5-aminosalicylic acid methyl ester.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated
  3. customThe resulting solid is separated
  4. washwashed with water
  5. washThe solid is then washed with ether
  6. customthe ether is evaporated to dryness
  7. customyielding a brown solid
  8. extractionThe aqueous filtrate above is extracted with ether
  9. dry with materialthe extract is dried over anhydrous sodium sulfate
  10. customevaporated
  11. customyielding a brown solid
  12. customrecrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-b81ed494e9ea4bc4968e388da24bf6d5
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04130660

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