Iodine → 7-Iodo-4-ethylisoindolinone

HRID 21188Notes

Reaction equation

HRID 21188 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH3:13])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:14].[K+].II.[N+]([O-])(OC(C)(C)C)=O>C(#N)C.[Cu](I)I>[I:14][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][CH3:13])=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 684909697-Amino-4-ethylisoindolinone

Product 1

HCID 684919467-Iodo-4-ethylisoindolinoneYield 50%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-ethylisoindolinone (46.0 mg, 0.260 mmol) was dissolved in acetonitrile (6.2 mL), and the solution was treated with potassium iodide (69.1 mg, 0.416 mmol), copper iodide (79.2 mg, 0.416 mmol), iodine (106 mg, 0.416 mmol) and tert-butyl nitrate (0.139 mL, 1.17 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1) to obtain 7-iodo-4-ethylisoindolinone (37.1 mg, yield 50%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1)

Sources & evidence

ORD record
ord-984a387cb3f94937a9bcf4b5064c2b1c
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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