Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate → Methyl 2-amino-5-(2-methoxyethoxy)benzoate

HRID 871318

Reaction equation

HRID 871318 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([N+:16]([O-])=O)=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]>[Pd].CO>[NH2:16][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 66639151Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate

Product 1

HCID 61305437Methyl 2-amino-5-(2-methoxyethoxy)benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To methyl 5-(2-methoxyethoxy)-2-nitrobenzoate (1.08 g, 4.2 mmol) under argon was added 10% Palladium on carbon and MeOH (20 mL). The flask was flushed with H2(g) and stirred under H2 (1 atm) for 30 minutes. The mixture was filtered through Celite and concentrated in vacuo to give methyl 2-amino-5-(2-methoxyethoxy)benzoate (964 mg, 4.2 mmol, 100%). LC-MS (ESI) m/z 226 (M+H)+.

Workup

  1. customThe flask was flushed with H2(g)
  2. filtrationThe mixture was filtered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a303abe4bb545b3854203e5b8f94033
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Linked notes

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