Water → HCID 22321258, compound

HRID 1377219Notes

Reaction equation

HRID 1377219 reaction equation
O.[N+:2]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)([O-])=O.[H][H]>[Pd].O1CCCC1>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=4)=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 962WaterHCID 22919105HCID 22919105, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22321258HCID 22321258, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 1-liter three-necked flask equipped with a stirring device and a nitrogen substituting device, 2.5 g of a Pd-C catalyst (a 5% product, containing 55.9% of water) and a solution of 25.1 g of 1,2-bis(4-(4-nitrobenzyl)phenyl)ethane in 400 milliliters of tetrahydrofuran were introduced and contacted with hydrogen gas at a normal pressure with stirring. After hydrogen absorption was stopped, the catalyst was filtered off and the solution was concentrated. Crystals were dissolved in chloroform, subjected to a column chromatography treatment with active alumina and silica gel, and thereafter the solution was reconcentrated to give a concentrate, which was then recrystallized from a toluene solvent, to obtain 13.7 g of 1,2-bis(4-(4-aminobenzyl)phenyl)ethane. Melting point was from 138.8° to 140.4° C.

Workup

  1. customIn a 1-liter three-necked flask equipped with a stirring device
  2. additionwere introduced
  3. customAfter hydrogen absorption
  4. filtrationthe catalyst was filtered off
  5. concentrationthe solution was concentrated
  6. dissolutionCrystals were dissolved in chloroform
  7. customto give a concentrate, which
  8. customwas then recrystallized from a toluene solvent

Sources & evidence

ORD record
ord-f13506b5cb464b83808cb1cf540e0187
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

Loading…