3-(Dihydroxyboranyl)-5-nitrobenzoic acid → 3-Amino-5-carboxybenzeneboronic acid

HRID 2081160Notes

Reaction equation

HRID 2081160 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([B:13]([OH:15])[OH:14])[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1)([O-])=O>C(O)C.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([B:13]([OH:15])[OH:14])[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=1

Participants

4

Reactant 1

HCID 27733153-(Dihydroxyboranyl)-5-nitrobenzoic acid

Product 1

HCID 27377953-Amino-5-carboxybenzeneboronic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-nitro-5-carboxyphenylboronic acid (3.3 g, 0.016 mol) in absolute ethanol (25 ml) was hydrogenated in the presence of Raney Nickel (1 g) at 50 lbs per square inch for 4 hours in a Parr shaker. The catalyst was removed by filtration and the solvent was removed on a rotary evaporator. The solid obtained was recrystallized from water. M.P. 210°-12° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed on a rotary evaporator
  3. customThe solid obtained
  4. customwas recrystallized from water

Sources & evidence

ORD record
ord-a056b2747fc642c888a1c555e1156aee
Source dataset
uspto-grants-1993_02
Patent number
US05183653

Reaction notes

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