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

HRID 350671Notes

Reaction equation

HRID 350671 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)amineYield 95.3%

Procedure

23.63 g (150 mmol) of 4-chloronitrobenzene are dissolved in 92.1 ml (1.38 mol) of ethylenediamine and heated to the boil under a nitrogen atmosphere. After 24 hours, the mixture is evaporated to dryness, and the crude product is suspended in 100 ml of 1 N sodium hydroxide solution and filtered off. Washing with water and drying under reduced pressure gives 25.9 g of N1-(4-nitrophenyl)ethane-1,2-diamine in the form of yellow crystals (ESI 182).

Workup

  1. temperatureheated to the boil under a nitrogen atmosphere
  2. customthe mixture is evaporated to dryness
  3. filtrationfiltered off
  4. washWashing with water
  5. customdrying under reduced pressure

Sources & evidence

ORD record
ord-69f26a2063fb41ce873e7d269010c612
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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