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 1098721Notes

Reaction equation

HRID 1098721 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-b5a21d8bd91149b7ba1da1af61e0196a
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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