Acetic Acid → 2-(Aminomethyl)aniline

HRID 580097Notes

Reaction equation

HRID 580097 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH:6]=[N:7]O)([O-])=O.C(O)(=O)C.[H][H].[OH-].[Na+]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][NH2:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 96097N-[(2-Nitrophenyl)methylidene]hydroxylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 1780962-(Aminomethyl)anilineYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

16.6 g (0.1 mol) of this o-nitrobenzaldoxime, 0.83 g of a 5% Pd-C catalyst, 12 g (0.2 mol) of glacial acetic acid and 100 ml of tetrahydrofurane were charged into a hermetically sealed glass container and stirred vigorously while charging hydrogen. Reaction was continued at temperatures of 25°-35° C. for 7 hours. After the reaction, the resulting mixture was filtered to remove the catalyst, was added with 8 g (0.2 mol) of sodium hydroxide and was subject to distillation. Thus, 9.7 g of o-aminobenzylamine was obtained. Yield 79.4%; Purity 99.4%; B.P. 91°-93° C./1 mmHg. M.P. 58°-61° C.

Workup

  1. customReaction
  2. customAfter the reaction
  3. filtrationthe resulting mixture was filtered
  4. customto remove the catalyst
  5. distillationwas subject to distillation

Sources & evidence

ORD record
ord-5120a784b172480c9d45fac5fb46e33c
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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