(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester → (4-Amino-phenoxy)-acetic acid 2-hydroxy-ethyl ester

HRID 501846Notes

Reaction equation

HRID 501846 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:17])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1>C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:17])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 59253945(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

Product 1

HCID 59253958(4-Amino-phenoxy)-acetic acid 2-hydroxy-ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4—Nitrophenoxy)-acetic acid-2-hydroxyethyl ester 23 (1 g, 4.15 mmol) was dissolved in ethyl acetate in a pressure vessel. Palladium on carbon (5%, 0.5 g) was added and the mixture stirred under an atmosphere of hydrogen (0.5 kg) for one hour. Catalyst was removed by filtration, the ethyl acetate distilled off and hexane added. The solid product was filtered and dried to give pure 28 (0.2 g 22.8%) as a brown powder with an m.p. between 104-106.3° C.

Workup

  1. customCatalyst was removed by filtration
  2. distillationthe ethyl acetate distilled off
  3. additionhexane added
  4. filtrationThe solid product was filtered
  5. customdried
  6. customto give pure 28 (0.2 g 22.8%) as a brown powder with an m.p. between 104-106.3° C.

Sources & evidence

ORD record
ord-ca400c4bbffe4195b8a428f6a41ceaca
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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