Salicylaldehyde → N,N'-Bis-(2-hydroxybenzyl)-m-xylylenediamine

HRID 65833

Reaction equation

HRID 65833 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:10]1([CH2:18][NH2:19])[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][NH2:17])[CH:11]=1>C(O)(C)C.[Ni]>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH2:1][NH:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:18][NH:19][CH2:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH:11]=1

Participants

5

Reactant 2

HCID 6998SalicylaldehydeHCID 151331,3-Benzenedimethanamine

Product 1

HCID 22756078N,N'-Bis-(2-hydroxybenzyl)-m-xylylenediamineYield 41.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

34.4 g of a bisazomethine prepared from 2 mols of salicylaldehyde and 1 mol of m-xylylenediamine and having a melting point of 61°-63° C. are hydrogenated for 7 hours in 170 ml of isopropanol in an autoclave in the presence of 4 g of Raney nickel at 85° C. and under a pressure of 60 atmospheres. The catalyst is filtered off and the filtrate is concentrated in a rotary evaporator to give 35.8 g of crude product. 25.7 g are recrystallised from 77 ml of isopropanol and the bulk of the product separates out on cooling in a refrigerator. The precipitate is collected by filtration, washed off with cold isopropanol and dried in vacuo at 40° C., affording 11.0 g (41.8% of theory) of N,N'-bis-(2-hydroxybenzyl)-m-xylylenediamine with a melting point of 67°-68° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in a rotary evaporator
  3. customto give 35.8 g of crude product
  4. custom25.7 g are recrystallised from 77 ml of isopropanol
  5. temperatureon cooling in a refrigerator
  6. filtrationThe precipitate is collected by filtration
  7. washwashed off with cold isopropanol
  8. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-3cf7519bbe4349b79ea103fe0719360e
Source dataset
uspto-grants-1978_12
Patent number
US04129556

Linked notes

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