2-((2-Methoxyethoxy)methoxy)-3-nitrobenzoic acid methyl ester → 3-Amino-2-((2-methoxyethoxy)methoxy)benzoic acid methyl ester

HRID 912429Notes

Reaction equation

HRID 912429 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19]

Participants

5

Reactant 2

HCID 582228052-((2-Methoxyethoxy)methoxy)-3-nitrobenzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 582228163-Amino-2-((2-methoxyethoxy)methoxy)benzoic acid methyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-((2-methoxyethoxy)methoxy)-3-nitrobenzoic acid methyl ester 5.0 g (17.5 mmol) of step 1 in methanol 50 mL was added 5% Pd/C 0.5 g, and the reactor was filled with hydrogen gas, after which the reaction mixture was stirred at room temperature for 24 hrs. The catalyst was removed off by celite filtration before concentrating the reaction mixture in a vacuum. Purification by column chromatography (developing solvent: ethylacetate/hexane=1/1) afforded 4.2 g of the title compound (yield 95%).

Workup

  1. customThe catalyst was removed off by celite filtration
  2. concentrationbefore concentrating the reaction mixture in a vacuum
  3. customPurification by column chromatography (developing solvent: ethylacetate/hexane=1/1)

Sources & evidence

ORD record
ord-5d60db39c2664666aa2039d962a96918
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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