Hydrochloric Acid → 2-Amino-5-chloro-4-nitrobenzoic acid

HRID 2405756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405756
C[O:2][C:3](=[O:15])[C:4]1[C:5](=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([Cl:11])[CH:10]=1)[NH2:6].[Li+].[OH-].Cl>C1COCC1.O>[Cl:11][C:9]1[CH:10]=[C:4]([C:3]([OH:15])=[O:2])[C:5]([NH2:6])=[CH:7][C:8]=1[N+:12]([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 20327955HCID 20327955, Verbindung

Produkt 1

HCID 214739642-Amino-5-chloro-4-nitrobenzoic acidAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-4-nitroanthranilic acid methyl ester (10.0 g, 43 mmol) in THF (120 mL) was added LiOH (2.7 g, 65 mmol) dissolved in water (40 mL). The reaction mixture was stirred at room temperature for 18 h and acidified to pH 4 with 1 N HCl. The aqueous layer was extracted with EtOAc (2×150 mL); the combined organic layers were dried over Na2SO4, filtered, and concentrated to give 5-chloro-4-nitroanthranilic acid (8.7 g, 88%) as an orange solid.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc (2×150 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-98c9499e795d4462a949d9e089f8be16
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809326B2

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