2-(4-Nitrophenoxy)naphthalene → 2-(4-Aminophenoxy)naphthalene

HRID 17712

Reaction equation

HRID 17712 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1>CCO.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 7624782-(4-Nitrophenoxy)naphthalene

Product 1

HCID 35808292-(4-Aminophenoxy)naphthalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitro intermediate (10 mmol) obtained above was dissolved in EtOH (50 mL) and hydrogenated in the presence of 10% Pd/C (300 mg) until completion according to General Procedure H, as indicated by TLC or HPLC. The reaction mixture was then filtered to remove the catalyst. The solvent was removed in vacuuo to afford the desired 4-(naphthalen-2-yloxy)aniline, which was used directly for further transformation without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-3a02678eca04486f9c195a6aa83690bd
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

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