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

HRID 864341Notes

Reaction equation

HRID 864341 reaction equation
[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]

Participants

4

Reactant 1

HCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 38010253-Amino-2-methylbenzoic acid methyl esterYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bf85983217c5422488f59ee711fdca69
Source dataset
uspto-grants-1996_10
Patent number
US05563138

Reaction notes

Loading…