Potassium Iodide → HCID 22624024, compound

HRID 279001Notes

Reaction equation

HRID 279001 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:23][N:24]1[C:33](=[O:34])[C:32]2[CH:35]=[C:36]([OH:38])[CH:37]=[C:30]3[C:31]=2[C:26](=[CH:27][CH:28]=[CH:29]3)[C:25]1=[O:39])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:23][N:24]1[C:33](=[O:34])[C:32]2[CH:35]=[C:36]([O:38][CH2:3][CH2:4][N:5]([CH3:7])[CH3:6])[CH:37]=[C:30]3[C:31]=2[C:26](=[CH:27][CH:28]=[CH:29]3)[C:25]1=[O:39])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 22624014HCID 22624014, compound

Product 1

HCID 22624024HCID 22624024, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-N,N-dimethylethylamine hydrochloride (0.5 g, 3.3 mmol), potassium iodide (0.4 g, 2.4 mmol), and potassium carbonate (1.4 g, 10.1 mmol) were added to a suspension of 2-benzyloxy-5-hydroxy-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.5 mmol) in acetone (100 mL). The mixture was refluxed for 8 hours and concentrated in vacuo. The residue was dissolved in water and extracted with 30% methanol in chloroform. The organic layer was dried (Na2SO4), filtered, and concentrated to give 0.3 g of 2-benzyloxy-5-(2-dimethylamino-ethoxy)-benzo[de]isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-5-(2-dimethylamino-ethoxy)-benzo[de]isoquinoline-1,3-dione (0.2 g) in the presence of 10% Pd/C (0.2 g) in DMA (20 mL) afforded 0.04 g of the title compound, mp 225-229° C.;

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with 30% methanol in chloroform
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dfd4442102dd48abbd430c4f068d0e14
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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