1,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl ester → Dimethyl 3-aminobenzene-1,2-dicarboxylate

HRID 9947

Reaktionsgleichung

Reaktionsgleichung von HRID 9947
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[C:13]([O:15][CH3:16])=[O:14].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[C:13]([O:15][CH3:16])=[O:14]

Komponenten

5

Edukt 2

HCID 2499121,2-Benzenedicarboxylic acid, 3-nitro-, 1,2-dimethyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl-2-(methoxycarbonyl)-3-nitrobenzoate (23.8 g, 99.51 mmol) in ethyl acetate (200 ml) was added 10% Pd/C (1.8 g). The mixture was hydrogenated under 50 psi of hydrogen for 3 hours in a Parr Type Shaker. The mixture was filtered through Celite and the filtrate was concentrated in vacuo to yield an oil. The crude product was purified by flash chromatography (dichloromethane/ethyl acetate 95 to 5) to afford 18.1 g (87%) of the product as a brown oil: 1H NMR (CDCl3) δ 7.22 (t, J=7.6 Hz, 1H), 6.90 (d, J=7.2 Hz, 1H), 6.79 (d, J=8.7 Hz), 5.07 (b, 2H), 3.85 (s, 3H), 3.83 (s, 3H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto yield an oil
  4. customThe crude product was purified by flash chromatography (dichloromethane/ethyl acetate 95 to 5)

Quellen und Nachweise

ORD-Eintrag
ord-02e4c90fbc514857ac01b7be488cb366
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091353B2

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