Ethylenediamine → N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)-ethylenediamine

HRID 1983560Notes

Reaction equation

HRID 1983560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13]Br)[CH:7]=[CH:6]2.[CH2:15]([NH2:18])[CH2:16][NH2:17].[C:19](=[O:22])([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH2:13][N:17]([CH2:13][C:8]1[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:22][CH3:19])[CH:4]=3)[N:9]=1)[CH2:16][CH2:15][N:18]([CH2:13][C:8]1[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=1)[CH2:13][C:8]1[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 216180432-(Bromomethyl)-6-methoxyquinoline

Product 1

HCID 11563958N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)-ethylenediamineYield 33.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-methoxy-2-bromomethylquinoline (0.076 g, 0.302 mmol), ethylenediamine (5 μL, 0.0755 mmol), potassium carbonate (0.125 g, 0.904 mmol) and acetonitrile (6 mL) was refluxed by heating for 14 hours. The solvent was evaporated under reduced pressure, and then the residue was separated by phase separation using chloroform and water. The organic layer was dried, and then the solvent was evaporated. The residue was washed with ethanol to obtain the objective compound as white powder (yield: 18.7 mg, 33%).

Workup

  1. temperaturewas refluxed
  2. temperatureby heating for 14 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was separated by phase separation
  5. customThe organic layer was dried
  6. customthe solvent was evaporated
  7. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-d0e37e11e41446fba83e46d0dff93694
Source dataset
uspto-grants-2009_06
Patent number
US07541467B2

Reaction notes

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