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

HRID 631277Notes

Reaction equation

HRID 631277 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-methoxyethoxyl)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-19564034fc134798bfb183c495d7b6f3
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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