Ethylenediamine → N-(2-aminoethyl)-N-(4-nitrophenyl)amine

HRID 37839Notes

Reaction equation

HRID 37839 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13]>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH2:12][CH2:11][NH2:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 74741-Chloro-4-nitrobenzene

Product 1

HCID 236318N-(2-aminoethyl)-N-(4-nitrophenyl)amine

Procedure

A mixture of 1-chloro-4-nitro-benzene (10 g, 64 mmol) and ethane-1,2-diamine (38 mL) was heated at reflux for 4 h. Excess ethane-1,2-diamine was evaporated under reduced pressure and water was added to the residue. The precipitated solid was filtered off and dried under vacuum to afford N*1*-(4-nitro-phenyl)-ethane-1,2-diamine (10.8 g, quantitative).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customExcess ethane-1,2-diamine was evaporated under reduced pressure and water
  4. additionwas added to the residue
  5. filtrationThe precipitated solid was filtered off
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ee3ffc2421374c7381eeaf4076dad9c7
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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