Water → HCID 59574309, compound

HRID 2092038Notes

Reaction equation

HRID 2092038 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[CH:6][CH:5]=[N:4][NH:3]1.[C:20](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:20][N:3]1[C:2](=[O:1])[C:7]([CH2:8][N:9]2[C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]2=[O:18])=[CH:6][CH:5]=[N:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 595748041H-Isoindole-1,3(2H)-dione, 2-[(2,3-dihydro-3-oxo-4-pyridazinyl)methyl]-

Product 1

HCID 59574309HCID 59574309, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(3-Oxo-2,3-dihydropyridazin-4-yl)methyl]isoindoline-1,3-dione (255 mg, 1.00 mmol) in dimethylformamide (3 mL) was heated with potassium carbonate (145 mg, 1.05 mmol) and methyl iodide (426 mg, 3.00 mmol) at 70° C. for 2 hours. After completion of the reaction, the solvent was removed by vacuum distillation, and the resulting residue was stirred with 4 M hydrogen chloride/1,4-dioxane (10 mL) at room temperature for 2 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (233 mg, 86% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by vacuum distillation
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-48127662b74b4fc8b5511337d6e04bbc
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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