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

HRID 1098726Notes

Reaction equation

HRID 1098726 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][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]>[NH2:1][C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:29])[CH:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=2)[CH3:18])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 592539882-(4-Nitrophenoxy)-propionic acid 2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester

Product 1

HCID 497643652-(4-Aminophenoxy)propionic acid-2-[2-(4-aminophenoxy)acetoxy]ethyl esterYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)acetoxy]-ethyl ester 38 (20 g, 50 mmol) was dissolved in dry dimethylformamide (150 ml) in a pressure vessel. Palladium on carbon (5%, 5 g) was added and the mixture stirred under an atmosphere of hydrogen (4 kg) for 3 hrs. The catalyst was removed by filtration and ice water (1 L) added to the filtrate. Crude 39 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using chloroform:ethyl acetate (8:2) to give pure 39 (10 g, 58%) as a dark brown syrup.

Workup

  1. customThe catalyst was removed by filtration and ice water (1 L)
  2. additionadded to the filtrate
  3. extractionCrude 39 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-d0cad6e652af4f79a3e2770bc418b502
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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