(4-Nitrophenoxy)-acetic acid-2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester → (4-Amino-phenoxy)-acetic acid-2-[2-(4-amino-phenoxy)-acetoxy]-ethyl ester

HRID 1038294Notes

Reaction equation

HRID 1038294 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:28])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)=[O:11])=[CH:6][CH:5]=1)([O-])=O>CN(C)C=O.[Ni]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:16]([O:15][CH2:14][CH2:13][O:12][C:10](=[O:11])[CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:30][CH:29]=2)=[O:28])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 59253942(4-Nitrophenoxy)-acetic acid-2-[2-(4-nitrophenoxy)-acetoxy]-ethyl ester

Product 1

HCID 25235089(4-Amino-phenoxy)-acetic acid-2-[2-(4-amino-phenoxy)-acetoxy]-ethyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound 2 (100 grams) was dissolved in 200 ml of dry dimethylformamide (DMF) in a pressure vessel followed by addition of 30 grams of Raney Nickel catalyst. The mixture was stirred under an atmosphere of hydrogen for about 10 hours. The disappearance of the starting material using TLC confirmed the completion of reaction. The catalyst was removed by filtration. About 80% of the DMF was distilled off under high vacuum. The compound was precipitated from the residual solution by addition to methanol to give 75 grams of pure 3 as an off-white powder. m.p: 182-185° C.

Workup

  1. customthe completion of reaction
  2. customThe catalyst was removed by filtration
  3. distillationAbout 80% of the DMF was distilled off under high vacuum
  4. customThe compound was precipitated from the residual solution by addition to methanol

Sources & evidence

ORD record
ord-36149bb50bb9402da64560d85ed4d597
Source dataset
uspto-grants-2013_10
Patent number
US08551519B2

Reaction notes

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