Methyl 2-ethoxy-4-nitrobenzoate → Methyl 4-amino-2-ethoxybenzoate

HRID 1807272

Reaction equation

HRID 1807272 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:2].[H][H]>[Pd].CO>[NH2:14][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:13]=1

Participants

5

Reactant 2

HCID 9964566Methyl 2-ethoxy-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67368855Methyl 4-amino-2-ethoxybenzoateYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-ethoxy-4-nitrobenzoate (2.038 g, 9.05 mmol) and palladium on carbon (583 mg, 10 wt %, Aldrich) in methanol (62 ml) was reacted with hydrogen at 40 psi for 18 hrs on the PARR shaker. It was filtered through celite and washed with methanol under N2 and the filtrate was concentrated to give methyl 4-amino-2-ethoxybenzoate (1.672 g, 94%) as a light brown solid.

Workup

  1. filtrationIt was filtered through celite
  2. washwashed with methanol under N2
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9acd94964bc04e788752929f301a7dac
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Linked notes

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