Ethanol → N-(4-{[(4-aminophenyl)amino]methyl}benzyl)benzene-1,4-diamine tetrahydrochloride

HRID 29732Notes

Reaction equation

HRID 29732 reaction equation
[Cl-:1].[NH4+].O.C(O)C.[N+:7]([C:10]1[CH:34]=[CH:33][C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)([O-])=O>CN1C(=O)CCC1.[Zn]>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([NH:23][CH2:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:13]3[CH:33]=[CH:34][C:10]([NH2:7])=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 236567624-nitro-N-(4-{[(4-nitrophenyl)amino]methyl}benzyl)aniline

Product 1

HCID 69252903N-(4-{[(4-aminophenyl)amino]methyl}benzyl)benzene-1,4-diamine tetrahydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of powdered zinc (22.2 g), ammonium chloride (2.5 g), water (4 ml) and absolute ethanol (20 ml) were brought to reflux with the oil bath. The 4-nitro-N-(4-{[(4-nitrophenyl)amino]methyl}benzyl)aniline (3.4 g) was dissolved in 20 ml of NMP and introduced dropwise until there was decoloration of the reaction medium, while at the same time the reflux was maintained.

Workup

  1. temperatureto reflux with the oil bath
  2. additionintroduced dropwise until there
  3. temperaturewhile at the same time the reflux was maintained

Sources & evidence

ORD record
ord-210702c204ef409592efd42d6c840278
Source dataset
uspto-grants-2008_09
Patent number
US07422609B2

Reaction notes

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