(3-Acetamido-2-nitrophenyl)boronic acid → [3-(Acetylamino)-2-aminophenyl]boronic acid

HRID 1518228Notes

Reaction equation

HRID 1518228 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:14]([O-])=O)=[C:7]([B:11]([OH:13])[OH:12])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]>CCO.[Pd]>[C:1]([NH:4][C:5]1[C:6]([NH2:14])=[C:7]([B:11]([OH:12])[OH:13])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 44119623(3-Acetamido-2-nitrophenyl)boronic acid

Product 1

HCID 53692531[3-(Acetylamino)-2-aminophenyl]boronic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

10% Pd on carbon (cat.) was added as a slurry in EtOH under N2 to [3-(acetylamino)-2-nitrophenyl]boronic acid in EtOH (0.05 M). The atmosphere in the reaction vessel was flushed with hydrogen (1 atm) and the reaction stirred vigorously at RT for 20 min. The hydrogen atmosphere was then replaced with N2 before filtering through a plug of CELITE—washing well with EtOH. The EtOH solution was concentrated in vacuo to afford the crude title compound as a brown solid, which was used immediately in the subsequent cross-coupling step. MS (ES+) m/z 195 (M+H)+.

Workup

  1. customThe atmosphere in the reaction vessel was flushed with hydrogen (1 atm)
  2. filtrationbefore filtering through a plug of CELITE—washing well with EtOH
  3. concentrationThe EtOH solution was concentrated in vacuo

Sources & evidence

ORD record
ord-31897acc693f42a2a19a39afabde5830
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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