(2-Nitrophenyl)boronic acid → (2-Aminophenyl)boronic acid

HRID 2224372Notes

Reaction equation

HRID 2224372 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[B:10]([OH:12])[OH:11])([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[B:10]([OH:12])[OH:11]

Participants

4

Reactant 1

HCID 2773548(2-Nitrophenyl)boronic acid

Product 1

HCID 2773216(2-Aminophenyl)boronic acidYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 84A (1.0 g, 6 mmol) and 10% Pd/C (50 mg) in EtOH (50 mL) was hydrogenated in a Paar shaker at 1 bar for 8 hours. The mixture was filtered through a pad of celite and the filtrate was concentrated. The resulting residue was triturated with hexanes and the resulting solid was filtered to afford 84B (0.4g, 50%).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was triturated with hexanes
  4. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-f487a1418f4742aaa22b6b91d3f396d1
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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