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

HRID 2190251Notes

Reaction equation

HRID 2190251 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>[Pd].CO>[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 44.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-nitrophenylboronic acid (500 mg, 2.99 mmol) and MeOH (10 mL) was added 10% Pd/C (250 mg). The mixture was stirred under hydrogen at atmospheric pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica, 0-50% CMA in CH2Cl2) to afford the sub-title compound (182 mg, 44%).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica, 0-50% CMA in CH2Cl2)

Sources & evidence

ORD record
ord-c672f3d941fb43459cad83ea1184df75
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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