Hydrochloric Acid → Methyl 2-amino-4-fluorobenzoate

HRID 3132

Reaktionsgleichung

Reaktionsgleichung von HRID 3132
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[C:13](=O)(O)[O-].[Na+]>CO.O>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 27249674-Fluoroanthranilic acid

Produkt 1

HCID 14075433Methyl 2-amino-4-fluorobenzoateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of 2-amino-4-fluorobenzoic acid (4.86 g, 31.3 mM) in anhydrous methanol (100 mL) was saturated with anhydrous hydrogen chloride and then refluxed for 4 days. During the reflux period, the reaction mixture was periodically resaturated with hydrogen chloride. After the reflux period, the reaction mixture was cooled and concentrated to leave a white solid. This material was dissolved in water and the resulting solution neutralized with aqueous sodium bicarbonate and extracted with diethyl ether. The combined extracts were dried (MgSO4), filtered and concentrated to leave (4.08 g, 80.6%) of the title compound as an off white solid, mp 66°-67° C.; MS(CI): 170 (M+H).

Aufarbeitung

  1. temperaturerefluxed for 4 days
  2. temperatureAfter the reflux period, the reaction mixture was cooled
  3. concentrationconcentrated
  4. customto leave a white solid
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fb1f425ed29c488e8ffdf69649ec7433
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733910

Verknüpfte Notizen

Wird geladen…