2-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester → 4-Amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester

HRID 1392260

Reaktionsgleichung

Reaktionsgleichung von HRID 1392260
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH:13][C:14](=[O:25])[C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:19][CH:20]=1

Komponenten

4

Edukt 1

HCID 691945292-(4-Tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester

Produkt 1

HCID 691966714-Amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl esterAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a Parr shaker bottle was added 10% Pd/C (0.346 g) then ethyl acetate (50 mL) followed by 2-(4-tert-butyl-benzoylamino)-4-nitro-benzoic acid methyl ester (3.041 g, 8.53 mmol) as a solution in ethyl acetate (200 mL). The reaction was hydrogenated overnight, filtered through celite and silica washing with ethyl acetate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80) to afford 4-amino-2-(4-tert-butyl-benzoylamino)-benzoic acid methyl ester (2.122 g, 76%) as a yellow solid.

Aufarbeitung

  1. filtrationfiltered through celite and silica washing with ethyl acetate
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-db6a674a07a8411f85ab16bd819a538b
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342039B2

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