1,2-Dichloro-4-nitrobenzene → N-(2-chloro-4-nitrophenyl)ethane-1,2-diamine

HRID 436339Notes

Reaction equation

HRID 436339 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.O.[CH2:13]([NH2:16])[CH2:14][NH2:15]>>[N+:9]([C:4]1[CH:5]=[CH:6][C:7]([NH:15][CH2:14][CH2:13][NH2:16])=[C:2]([Cl:1])[CH:3]=1)([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 12200817Ethylenediamine monohydrate

Product 1

HCID 2829584N-(2-chloro-4-nitrophenyl)ethane-1,2-diamineYield 95.1%

Procedure

192 g (1mole) of 3,4-dichloro-nitrobenzene is added to 810 cm3 (10 moles) ethylene diamine hydrate. The reaction mixture is heated at reflux for 4 hours and then poured into 2.5 liters of ice water. Drying yields 205 g of 4-nitro-2-chloro-N-(β-aminoethyl) aniline which, after recrystallization in absolute ethanol, melts at 116° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. customDrying

Sources & evidence

ORD record
ord-21bfa5ace67b4bf3916f890793f96f57
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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