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

HRID 496106Notes

Reaction equation

HRID 496106 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 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-nitrophenylboronic acid (2 g; 12 mmol) and 5% Pd/C (100 mg) in EtOH (100 ml) was hydrogenated at 1 bar until TLC indicated complete conversion of starting material. The reaction mixture was filtered through celite and the filtrate evaporated to dryness. The remanense was washed with hexane and filtered to give 900 mg of (55%) 2-aminophenylboronic acid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated to dryness
  3. washThe remanense was washed with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5ee4f7cbbf5a4a35b02b27e734107152
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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