Iodine → HCID 68489346, compound

HRID 21091Notes

Reaction equation

HRID 21091 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:18].[K+].II.N(OC(C)(C)C)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.[Cu](I)I>[I:18][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

8

Reactant 5

HCID 807IodineHCID 4875Potassium IodideHCID 10906Tert-Butyl nitrite2×HCID 24477Sodium ThiosulfateHCID 684906311h-Isoindol-1-one,7-amino-2,3-dihydro-4-phenyl-

Product 1

HCID 68489346HCID 68489346, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

  1. temperaturecooling for 1.5 hours
  2. stirringby stirring at 50° C. for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=6/1)

Sources & evidence

ORD record
ord-47dabac025ea44c996c54a188a8ea5dc
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

Loading…