Potassium Hydroxide → HCID 9830525, compound

HRID 1941260Notes

Reaction equation

HRID 1941260 reaction equation
[C:1]1(=[O:19])[C:10]2[C:5]3[C:6](=[CH:15][CH:16]=[CH:17][C:4]=3[C:3](=[O:18])[NH:2]1)[CH:7]=[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]1=2.[OH-:20].[K+].Br[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31]Br>C(O)C>[O:19]=[C:1]1[C:10]2[C:5]3[C:6](=[CH:15][CH:16]=[CH:17][C:4]=3[C:3](=[O:18])[N:2]1[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH:29][CH2:30][CH2:31][N:2]1[C:3](=[O:20])[C:4]3[CH:17]=[CH:16][CH:15]=[C:6]4[C:5]=3[C:10](=[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]3=[CH:7]4)[C:1]1=[O:19])[CH:7]=[C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]1=2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 15488322HCID 15488322, compoundHCID 21460421N,N'-bis(2-bromoethyl)-1,3-propanediamine

Product 1

HCID 9830525HCID 9830525, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A mixture of 1.23 g (5 mmol) of 1,2-dihydro-3H-dibenz[de,h]isoquinoline-1,3-dione in 100 ml of ethanol is treated with 280 mg (5 mmol) of potassium hydroxide in 50 ml of ethanol. After refluxing for 3 hours, 0.65 g (2.5 mmol) of N,N'-bis(2-bromoethyl)-1,3-propanediamine in 50 ml of ethanol are added and the whole is refluxed for 24 hours. The reaction mixture is concentrated in vacuo. The residue is treated with water (100 ml) and extracted with dichloromethane. The organic layers are combined, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed, eluting with dichloromethane, methanol, acetic acid (80:15:5). The appropriate fractions are combined, concentrated in vacuo and crystallized from toluene to give 0.31 g (20%) of N,N'-bis[2-(1,2-dihydro-1,3-dioxo-3H-dibenz[de,h]isoquinolin-2-yl)ethyl]-1,3-propanediamine. M.p. 191° C.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. temperaturethe whole is refluxed for 24 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. additionThe residue is treated with water (100 ml)
  5. extractionextracted with dichloromethane
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed
  10. washeluting with dichloromethane, methanol, acetic acid (80:15:5)
  11. concentrationconcentrated in vacuo
  12. customcrystallized from toluene

Sources & evidence

ORD record
ord-08641965e68c4cc8997d0f3a59484177
Source dataset
uspto-grants-1997_12
Patent number
US05703089

Reaction notes

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