Methyl 2-chloro-3-nitrobenzoate → Methyl 3-amino-2-chlorobenzoate

HRID 51343

Reaktionsgleichung

Reaktionsgleichung von HRID 51343
[H][H].[Cl:3][C:4]1[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>C(OCC)(=O)C.[Pt]>[Cl:3][C:4]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 2

HCID 10751184Methyl 2-chloro-3-nitrobenzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 15132848Methyl 3-amino-2-chlorobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Hydrogen gas was passed through a solution of methyl 2-chloro-3-nitrobenzoate (10.0 g, 46.4 mM) and 1.0 g of 3% sulfided platinum on carbon in 150 mL ethyl acetate for 48 hours at room temperature. The catalyst was removed by filtration through celite. Concentration of the filtrate afforded 8.6 g (100%) of methyl 2-chloro-3-aminobenzoate as a yellow oil. 1H NMR (CDCl3) δ7.25 (dd, 1H, J=1 and 8 Hz), 7.2 (t, 1H, J=8 Hz), 6.95 (dd, 1H, J=1 and 8 Hz), and 3.9 (s, 3H). IR (CHCl3, cm−1) 3450, 3380, 2980, 2900, 1729, 1615, 1456, 1434, 1322, 1290, and 1268. MS (ES) m/e 186, 188.

Aufarbeitung

  1. customThe catalyst was removed by filtration through celite

Quellen und Nachweise

ORD-Eintrag
ord-83726865fea548679b1ef635088771de
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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