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

HRID 5372

Reaktionsgleichung

Reaktionsgleichung von HRID 5372
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 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester (2.75 g, 10.6 mmol) 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. The aqueous solution was extracted with ether (20 mL) and acidified 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 (75%) of 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-1be6548ad9b94f2f8afd6c1d75cd9889
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244907

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