Reaktion #9593

ord-a763b5a33d5f4a50b6f144f670dad872

Reaktionsgleichung

O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl
7-bromo-4-chloro-3-nitroquinoline
NCCN
ethylenediamine
NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12
N1-(7-bromo-3-nitroquinolin-4-yl)ethane-1,2-diamine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction was quenched with 2 L water
  2. 2
    workup.STIRRINGstirred for an additional hour
  3. 3
    workup.ADDITIONAdditional water was added
  4. 4
    workup.STIRRINGthe mixture was stirred overnight
  5. 5
    SonstigeA precipitate formed
  6. 6
    Sonstigewas isolated by filtration
  7. 7
    Sonstigeair-dried overnight on the filter funnel

Vorschrift

A solution of 7-bromo-4-chloro-3-nitroquinoline (143.8 g, 0.5 mol) in 800 mL warm DMF was added to a stirred solution of ethylenediamine in 200 mL DMF at room temperature; the reaction was stirred at room temperature overnight. The reaction was quenched with 2 L water and stirred for an additional hour. Additional water was added, and the mixture was stirred overnight. A precipitate formed and was isolated by filtration and air-dried overnight on the filter funnel to provide N1-(7-bromo-3-nitroquinolin-4-yl)ethane-1,2-diamine as a yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091214B2uspto-grants-2006_08