Carbon Dioxide → 3-Aminobenzylamine

HRID 580091Notes

Reaction equation

HRID 580091 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8]O)([O-])=O.C(=O)=O.[H][H].[OH-].[Na+]>[Ni].CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][NH2:8]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 2191323-NitrobenzaldoximeHCID 178418361HCID 178418361, compound

Product 1

HCID 46288313-AminobenzylamineYield 86.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

16.6 g (0.1 mol) of this m-nitrobenzaldoxime, 22 g (0.5 mol) of a solid CO2, 1 g of Raney nickel catalyst and 150 ml of methanol were charged into an autoclave and hydrogen was charged while maintaining the pressure at 20 to 30 Kg/cm2 ·G. Reaction was continued at temperatures of 20° to 25° C. for 8 hours under stirring. Thereafter, the resulting mixture was filtered to remove the catalyst, added with 6 g (0.15 mol) of sodium hydroxide and was subject to distillation. 10.6 g of m-aminobenzylamine of 99.1% in purity by means of gas chromatography was obtained. Yield 86.9%; B.P. 129°-130° C./5 mmHg; M.P. 39°-42° C.

Workup

  1. additionwas charged
  2. temperaturewhile maintaining the pressure at 20 to 30 Kg/cm2 ·G
  3. customReaction
  4. filtrationThereafter, the resulting mixture was filtered
  5. customto remove the catalyst
  6. distillationwas subject to distillation

Sources & evidence

ORD record
ord-bd9b1b824c16445695181b66f6efb313
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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