3-(4-Nitrophenoxy)benzoic acid → 3-(4-Aminophenoxy)benzoic acid

HRID 491074

Reaction equation

HRID 491074 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)([OH:3])=[O:2]>CO.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 7679193-(4-Nitrophenoxy)benzoic acid

Product 1

HCID 230090363-(4-Aminophenoxy)benzoic acidYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 4-(3-carboxyphenoxy)-1-nitrobenzene (5.38 g, 20.7 mmol) and 10% Pd/C (0.50 g) in MeOH (120 mL) was stirred under an H2 atmosphere (balloon) for 2 d. The resulting mixture was filtered through a pad of Celite®, then concentrated under reduced pressure to afford 4-(3-carboxyphenoxy)aniline as a brown solid (2.26 g, 48%): TLC (10% MeOH/90% CH2Cl2) Rf0.44 (streaking).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-997a3e82a225452f878e5f94ee5d3a02
Source dataset
uspto-grants-2009_05
Patent number
US07528255B2

Linked notes

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