Methyl 4-methoxy-2-nitrobenzoate → Methyl 2-amino-4-methoxybenzoate

HRID 1672176

Reaction equation

HRID 1672176 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:13]([O-])=O)[CH:4]=1>CO>[NH2:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 1

HCID 17733355Methyl 4-methoxy-2-nitrobenzoate

Product 1

HCID 12919999Methyl 2-amino-4-methoxybenzoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-methoxy-2-nitrobenzoate (9.0 g, 43 mmol) in MeOH (100 mL) was degassed and purged with nitrogen. To this solution was added 10% palladium hydroxide on carbon (1.2 g). The reaction mixture was degassed, purged with hydrogen and allowed to stir at rt overnight. The reaction mixture was filtered through Celite®, the Celite was washed with MeOH and the filtrate was concentrated to give methyl 2-amino-4-methoxybenzoate (7.80 g, 76%) as a brown solid. LCMS (FA): m/z=182.1 (M+H).

Workup

  1. custompurged with nitrogen
  2. additionTo this solution was added 10% palladium hydroxide on carbon (1.2 g)
  3. customThe reaction mixture was degassed
  4. custompurged with hydrogen
  5. filtrationThe reaction mixture was filtered through Celite®
  6. washthe Celite was washed with MeOH
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ff6619b325b449f299c28f0c8caa87fe
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Linked notes

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