Ethylenediamine → HCID 67067110, compound

HRID 2174636Notes

Reaction equation

HRID 2174636 reaction equation
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=O.[CH2:20]([NH2:23])[CH2:21][NH2:22]>[Cl-].[Na+].O>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:6]([C:4]2[C:3]3[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=3[NH:23][CH2:20][CH2:21][N:22]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 49762430HCID 49762430, compound

Product 1

HCID 67067110HCID 67067110, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

3-(2-Bromobenzoyl)quinoline (10.30 g, 33.0 mmol) was added to 100 mL of ethylene diamine, followed by stirring at 100° C. for 18 hours. Then the resulting reaction solution was cooled to room temperature, and poured into brine, followed by extracting with ethyl acetate. The organic layer was washed with brine twice, followed by drying with magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=9:1) to obtain the target compound (1.19 g, yield: 13%).

Workup

  1. customThen the resulting reaction solution
  2. temperaturewas cooled to room temperature
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with brine twice
  5. dry with materialby drying with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-3adc9bdf7557425bad352b982dd164da
Source dataset
uspto-grants-2015_06
Patent number
US09062024B2

Reaction notes

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