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

HRID 1957851Notes

Reaction equation

HRID 1957851 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 esterYield 22.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(4-Aminophenoxy)acetic acid methyl ester 41 (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 was stirred under an atmosphere of hydrogen (0.5 Kg) for one hour. The catalyst was removed by filtration, ethyl acetate was distilled off and hexane was added. The solid product was filtered and dried to give pure 46 (0.2 g, 22.8%) as a brown powder. M.p: 104-106.3° C.

Workup

  1. customThe catalyst was removed by filtration, ethyl acetate
  2. distillationwas distilled off
  3. additionhexane was added
  4. filtrationThe solid product was filtered
  5. customdried

Sources & evidence

ORD record
ord-f716176133be4fa3bc40ae584ace98cd
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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