Bis(2-hydroxybenzyl)-4-(p-nitrobenzyl)diethylenetriamine → Bis(2-hydroxybenzyl)-4-(p-aminobenzyl)diethylenetriamine

HRID 1608464Notes

Reaction equation

HRID 1608464 reaction equation
[OH:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][N:5]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29])[CH2:6][CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[CH2:9][CH2:10][NH2:11]>C(O)C.[Pd]>[OH:1][C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][N:5]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29])[CH2:6][CH2:7][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1)[CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 1

HCID 20085907Bis(2-hydroxybenzyl)-4-(p-nitrobenzyl)diethylenetriamine

Product 1

HCID 20085910Bis(2-hydroxybenzyl)-4-(p-aminobenzyl)diethylenetriamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 40 mL of absolute ethanol was dissolved 400 mg of bis(2-hydroxybenzyl)-4-(p-nitrobenzyl)diethylenetriamine (prepared in Example 1) and 100 mg of palladium on activated charcoal (10% Pd). The mixture was hydrogenated at 40 psi (275.8 kPa) for 24 hours. The catalyst was removed by filtration. The ethanolic solution was evaporated to provide bis(2-hydroxybenzyl)-4-(p-aminobenzyl)diethylenetriamine, and was characterized by: 1H NMR (CDCl3), carbon protons only; amine and hydroxyl protons were not included: δ 2.6 (s, 8H), 3.4 (s, 2H), 3.8 (s, 4H), 6.4-7.2 (m, 12H). 13C NMR (CDCl3) δ 46.06, 52.35, 53.48, 58.74, 115.08, 116.33, 118.87, 122.50, 128.35, 128.62, 130.03, 145.74, 158.31.

Workup

  1. customThe catalyst was removed by filtration
  2. customThe ethanolic solution was evaporated

Sources & evidence

ORD record
ord-26d5055318b8468fb3a292d2829b4a1b
Source dataset
uspto-grants-1995_03
Patent number
US05395608

Reaction notes

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