Methyl 2-methyl-5-nitrobenzoate → Methyl 5-Amino-2-methylbenzoate

HRID 8955

Reaktionsgleichung

Reaktionsgleichung von HRID 8955
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[CH3:13]>[Pd].CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[CH3:13]

Komponenten

4

Edukt 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate

Produkt 1

HCID 15049977Methyl 5-Amino-2-methylbenzoateAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-5-nitro-benzoic acid methyl ester (1.50 g, 7.8 mmol) in 4:1 MeOH/EtOAc (20 mL) was shaken at room temperature with a suspension of 10% Pd/C (175 mg, 0.17 mmol) under hydrogen atmosphere (35 psi) for 17 h. The catalyst was removed by filtration over celite, and the filtrate was concentrated in vacuo to give a pale yellow oil (1.29 g, 99%). 1H NMR (CDCl3) δ 2.46 (s, 3H), 3.63 (br s, 2H), 3.87 (s, 3H), 6.74 (dd, 1H, J=9.0, 3.0 Hz), 7.02 (d, 1H, J=6.0 Hz), 7.25 (d, 1H, J=3.0 Hz).

Aufarbeitung

  1. customThe catalyst was removed by filtration over celite
  2. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f389573b6e7429ebe8c788e377a0f58
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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