2-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl ester → 2-(4-Aminophenoxy)-propionic acid 2-[2-(4-aminophenoxy)-propionyloxy]-ethyl ester

HRID 501850Notes

Reaction equation

HRID 501850 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][CH:9]([CH3:30])[C:10]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:29])[CH:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[CH3:18])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CN(C)C=O.[Pd]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH:17]([CH3:18])[C:16]([O:15][CH2:14][CH2:13][O:12][C:10](=[O:11])[CH:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:32][CH:31]=2)[CH3:30])=[O:29])=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 592539622-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl ester

Product 1

HCID 497643642-(4-Aminophenoxy)-propionic acid 2-[2-(4-aminophenoxy)-propionyloxy]-ethyl esterYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4—Nitrophenoxy)-propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]-ethyl ester 31 (50 g, 89.3 mmol) was dissolved in dry dimethylformamide (400 ml) in a pressure vessel. Palladium on carbon(5%, 12.5 g) was added, and the mixture stirred under an atmosphere of hydrogen (4 kg) for 4 hours. Catalyst was removed by filtration and ice water (3 L) was added to the filtrate. Crude 32 was extracted into ethyl acetate, dried over Na2SO4, and distilled and purified by column chromatography on silica gel using chloroform as eluant to give pure 32 (25 g, 58%) as a syrup.

Workup

  1. customCatalyst was removed by filtration and ice water (3 L)
  2. additionwas added to the filtrate
  3. extractionCrude 32 was extracted into ethyl acetate
  4. dry with materialdried over Na2SO4
  5. distillationdistilled
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8d8e30899016441f9b1a510a5b1fa594
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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