Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

HRID 1458698Notes

Reaction equation

HRID 1458698 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:6]([O:8][CH3:9])=[O:7]>CO.O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[NH2:13])[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 1

HCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 602411Methyl 4-amino-3-methoxybenzoateYield 93.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-methoxy-4-nitrobenzoate (4.8 g; 23 mmol) was dissolved in 150 ml of a 2:1 mixed solvent of methanol and tetrahydrofuran, followed by addition of 480 mg of 5% Pd/C. The resulting mixture was stirred for 2 hours under a hydrogen gas atmosphere at room temperature. After completion of the reaction, the Pd/C was filtered off and the solvent was distilled out under reduced pressure, whereby 3.9 g of white crystals were obtained (yield: 54%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe Pd/C was filtered off
  3. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-45ef4e35b3a2446881fb8ea6921f8d99
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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