Boric Acid → 3-Aminobenzylamine

HRID 580087Notes

Reaction equation

HRID 580087 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.B(O)(O)O>[Ni].O1CCOCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][NH2:8]

Participants

5

Reactant 2

HCID 7628Boric AcidHCID 2191323-Nitrobenzaldoxime

Product 1

HCID 46288313-AminobenzylamineYield 86.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

33.2 g (0.2 mol) of m-nitrobenzaldoxime obtained in Example 2, 3 g of Raney nickel, 30.9 g (0.5 mol) of boric acid and 150 ml of dioxane were charged into an autoclave and reaction was effected at 30° C. under a hydrogen pressure of 10 Kg/cm2 ·G for five hours while vigorously stirring. After completion of the reaction, the resulting mixture was filtered to remove the catalyst, concentrated under reduced pressure and thereafter, was subject to the same post-treatment as in Example 1. 21.1 g of m-aminobenzylamine of 99.96% in purity was obtained. Yield 86.3%; B.P. 131°-132° C./6 mmHg).

Workup

  1. customwas effected at 30° C. under a hydrogen
  2. custom·G for five hours
  3. customAfter completion of the reaction
  4. filtrationthe resulting mixture was filtered
  5. customto remove the catalyst
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4d78f8a1c794822b335558ec3c6845b
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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