N-Methoxy-1-(2-nitrophenyl)methanimine → Benzaldehyde, 2-amino-, O-methyloxime

HRID 1729031Notes

Reaction equation

HRID 1729031 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>C(O)C.[Pd]>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]=[N:3][O:2][CH3:1]

Participants

4

Reactant 1

HCID 555699N-Methoxy-1-(2-nitrophenyl)methanimine

Product 1

HCID 54181456Benzaldehyde, 2-amino-, O-methyloxime

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(N-methoxyiminomethyl)-nitrobenzene (6.5 g) in 350 ml 99.9% ethanol was reduced catalytically at room temperature, 1 atm. using 0.7 g 10% Pd on carbon. Upon completion of the reduction the solution was filtered throughfilter aid and concentrated in vacuo. The product was redissolved in methylene chloride and filtered through silicagel. Evaporation of the solvent gave the desired product as an oil.

Workup

  1. customwas reduced catalytically at room temperature
  2. filtrationUpon completion of the reduction the solution was filtered throughfilter aid
  3. concentrationconcentrated in vacuo
  4. dissolutionThe product was redissolved in methylene chloride
  5. filtrationfiltered through silicagel
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b044038a1ed3402098ecefd7a41cafe3
Source dataset
uspto-grants-1994_07
Patent number
US05330990

Reaction notes

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