Methyl 2-methyl-3-nitrobenzoate → 3-Amino-2-methylbenzoic acid methyl ester

HRID 1285

Reaktionsgleichung

Reaktionsgleichung von HRID 1285
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(O)(=O)C.[Pd]>[CH3:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

4

Edukt 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Produkt 1

HCID 38010253-Amino-2-methylbenzoic acid methyl esterAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Methyl 2-methyl-3-nitrobenzoate (10.0 g) is dissolved in acetic acid (50 ml) and thereto 5% Pd-C (1 g) is added to carry out catalytic reduction at room temperature under 1 atm. After 1.5 hours, the catalyst is filtered off. The reaction mixture is concentrated, and thereto is added water, and the mixture is made alkaline with potassium carbonate, followed by extraction with dichloromethane. The solvent is concentrated to give methyl 2-methyl-3-aminobenzoate (8.6 g).

Aufarbeitung

  1. customat room temperature
  2. filtrationthe catalyst is filtered off
  3. concentrationThe reaction mixture is concentrated
  4. additionis added water
  5. extractionfollowed by extraction with dichloromethane
  6. concentrationThe solvent is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a382dee7401645edb9da6c1fce7078a0
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723648

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