Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Tert-Butyl nitrite | HCID 10906 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | 1h-Isoindol-1-one,7-amino-2,3-dihydro-4-phenyl- | HCID 68490631 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68489346 | HCID 68489346 | 61% |
Reaction Steps
7-Amino-4-phenylisoindolinone (80.0 mg, 0.357 mmol) was dissolved in acetonitrile (4.8 mL), and the solution was added with potassium iodide (71.0 mg, 0.428 mmol), copper iodide (82.0 mg, 0.428 mmol), iodine (109 mg, 0.428 mmol) and tert-butyl nitrite (0.068 mL, 0.57 mmol), followed by stirring under ice-cooling for 1.5 hours. Then, the reaction mixture was warmed to room temperature and further added with tert-butyl nitrite (0.068 mL, 0.57 mmol), followed by stirring at 50° C. for 1.5 hours. The reaction mixture was added with 10% aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=6/1) to obtain 7-iodo-4-phenylisoindolinone (72.6 mg, yield 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07745641B2 |
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| Source dataset | uspto-grants-2010_06 |
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| ORD ID | ord-47dabac025ea44c996c54a188a8ea5dc |
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| Source note | uspto-grants-2010_06 |
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