Ethyl 2-methyl-5-nitrobenzoate → Ethyl 5-amino-2-methylbenzoate

HRID 1640010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640010
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([CH3:1])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

4

Edukt 1

HCID 18510875Ethyl 2-methyl-5-nitrobenzoate

Produkt 1

HCID 18690998Ethyl 5-amino-2-methylbenzoateAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-methyl-5-nitrobenzoate (11.5 g, 54 mmol) and 10% Pd/C (1.2 g) in ethanol (200 mL) was shaken under an atmosphere of hydrogen at 40 psi for 18 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure to provide ethyl 5-amino-2-methylbenzoate (9.77 g, 98%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.25 (d, J=2.6 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 6.74 (d, J=8.1 Hz, 1H), 4.33 (q, J=7.2 Hz, 2H), 2.46 (s, 3H), 1.38 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. filtrationAfter this time, the mixture was filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c36d299c9b44339b779d02427b7699a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110681B2

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