Ethylenediamine → N1-(7-bromo-3-nitroquinolin-4-yl)ethane-1,2-diamine

HRID 9497Notes

Reaction equation

HRID 9497 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:16]([NH2:19])[CH2:17][NH2:18]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:18][CH2:17][CH2:16][NH2:19])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 219843617-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 86593770N1-(7-bromo-3-nitroquinolin-4-yl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  1. customThe reaction was quenched with 2 L water
  2. stirringstirred for an additional hour
  3. additionAdditional water was added
  4. stirringthe mixture was stirred overnight
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. customair-dried overnight on the filter funnel

Sources & evidence

ORD record
ord-a763b5a33d5f4a50b6f144f670dad872
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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