Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid

HRID 846601

Reaktionsgleichung

Reaktionsgleichung von HRID 846601
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].[OH-].[Na+].O>C(O)C>[NH2:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 539320764-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

Produkt 1

HCID 197959774-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the ester (2.75 g, 0.0106 mole) in 95% ethanol (20 ml) was treated with 50% sodium hydroxide (10 ml) and water (10 ml), and refluxed for one hour. The ethanol was removed in vacuo and replaced with water, and the aqueous solution was extracted with ether (20 ml) and adjusted to pH~4 with concentrated hydrochloric acid (16 ml). A solid soon precipitated, and this was filtered, washed with water, air dried, and recrystallized from ethyl acetate (2 crops) to afford 2.03 g (78%) of the title compound as fine pale tan needles; mp 119°-120° C.

Aufarbeitung

  1. temperaturerefluxed for one hour
  2. customThe ethanol was removed in vacuo
  3. extractionthe aqueous solution was extracted with ether (20 ml)
  4. customA solid soon precipitated
  5. filtrationthis was filtered
  6. washwashed with water, air
  7. customdried
  8. customrecrystallized from ethyl acetate (2 crops)

Quellen und Nachweise

ORD-Eintrag
ord-883d96e6799b4a57ada5dddcba134dae
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137895

Verknüpfte Notizen

Wird geladen…