2-Methoxy-5-nitro-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide → 5-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 1634519

Reaktionsgleichung

Reaktionsgleichung von HRID 1634519
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:6]>[Pd].C(OCC)(=O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH:19]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:17])([F:18])[F:16])=[CH:13][CH:14]=1)=[O:6]

Komponenten

4

Edukt 1

HCID 110573402-Methoxy-5-nitro-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide

Produkt 1

HCID 109034245-amino-2-methoxy-N-(4-trifluoromethylbenzyl)benzamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Methoxy-5-nitro-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide (14.6 g, 41.2 mmol) and 146 ml of ethyl acetate were mixed and, after 10% palladium on activated carbon (2.6 g) was added, the mixture was stirred for 5 hours at room temperature. Catalyst was filtered, washed with ethyl acetate, and the reaction mixture was concentrated. The residue was recrystallized from a mixed solvent of n-hexane with ethyl acetate to obtain 12.4 g (93%) of the title compound as colorless crystals.

Aufarbeitung

  1. filtrationCatalyst was filtered
  2. washwashed with ethyl acetate
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was recrystallized from a mixed solvent of n-hexane with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2149c055c29b426ea44d3066bb468b82
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506797B1

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