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

HRID 83799Notes

Reaction equation

HRID 83799 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-04e09bd4ce414c88a8d2d8eafc30e212
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Reaction notes

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