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

HRID 1917716Notes

Reaction equation

HRID 1917716 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-0129dbf136b145cf97f3c5e1b976abcb
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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