Ethyl 2-(3-nitrophenoxy)acetate → Ethyl 2-(3-aminophenoxy)acetate

HRID 450053

Reaction equation

HRID 450053 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 2741030Ethyl 2-(3-nitrophenoxy)acetate

Product 1

HCID 412308Ethyl 2-(3-aminophenoxy)acetateYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3-nitrophenoxy)-acetic acid ethyl ester (500 mg, 2.22 mmol) in methanol (20 ml) was hydrogenated over 10% Pd—C (50 mg) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to yield a residue which was purified over neutral alumina using ethyl acetate-hexane to give (3-amino-phenoxy)-acetic acid ethyl ester (330 mg, 77%) as oil.

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated
  3. customto yield a residue which
  4. customwas purified over neutral alumina

Sources & evidence

ORD record
ord-56698f46ec324d218ba3f9e3adbc8585
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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