Methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate → Methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate

HRID 883819

Reaktionsgleichung

Reaktionsgleichung von HRID 883819
C([O:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:10]=1[Cl:27])C1C=CC=CC=1>[Pd].C1COCC1>[Cl:15][C:14]1[CH:13]=[C:12]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH:11]=[C:10]([Cl:27])[C:9]=1[OH:8]

Komponenten

4

Edukt 1

HCID 59509768Methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate

Produkt 1

HCID 59509759Methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Palladium on carbon (10% by mass of 10% by wt Pd, 50 mg) was cautiously added to a deoxygenated stirring solution of methyl 2-(4-(benzyloxy)-3,5-dichlorophenylamino)benzoate (0.520 g, 1.3 mmol) in THF (15 mL). The mixture was subjected to three cycles of evacuation and purging with hydrogen gas, before being stirred under an atmosphere of hydrogen gas. After 3 h, the reaction was purged with nitrogen, filtered through Celite™ (eluent: THF) and concentrated in vacuo to afford methyl 2-(3,5-dichloro-4-hydroxyphenylamino)benzoate as a white solid that was used without further purification.

Aufarbeitung

  1. custompurging with hydrogen gas
  2. customthe reaction was purged with nitrogen
  3. filtrationfiltered through Celite™ (eluent: THF)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7bde8d590a624b9e8e29c4ca16a04b98
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236984B2

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