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

HRID 1285

Reaction equation

HRID 1285 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-a382dee7401645edb9da6c1fce7078a0
Source dataset
uspto-grants-1998_03
Patent number
US05723648

Linked notes

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