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

HRID 2169729Notes

Reaction equation

HRID 2169729 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-5d2e28c1e50e4a9da0203d0da6b6d234
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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