Iodine → 7-Iodo-2,3-dihydro-1H-isoindol-1-one

HRID 21190Notes

Reaction equation

HRID 21190 reaction equation
NC1C=CC(C)=C2C=1C(=O)NC2.NC1C=CC=C2C=1C(=O)NC2.[I-].[K+].II.[N+]([O-])(OC(C)(C)C)=O.[I:36][C:37]1[CH:38]=[CH:39][C:40](C)=[C:41]2[C:45]=1[C:44](=[O:46])[NH:43][CH2:42]2>C(#N)C.[Cu](I)I>[I:36][C:37]1[CH:38]=[CH:39][CH:40]=[C:41]2[C:45]=1[C:44](=[O:46])[NH:43][CH2:42]2

Participants

9

Reactant 6

HCID 807IodineHCID 4875Potassium IodideHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 162289237-Amino-2,3-dihydro-1H-isoindol-1-oneHCID 534386827-Amino-4-methylisoindolin-1-oneHCID 684890937-Iodo-4-methylisoindolinone

Product 1

HCID 469118897-Iodo-2,3-dihydro-1H-isoindol-1-oneYield 50%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, a mixture of 7-amino-4-methylisoindolinone and 7-aminoisoindolinone (10/1, 57.4 mg, 0.357 mmol) was dissolved in acetonitrile (4.6 mL), and the solution was treated with potassium iodide (78 mg, 0.47 mmol), copper iodide (90 mg, 0.47 mmol), iodine (120 mg, 0.471 mmol) and tert-butyl nitrate (0.128 mL, 1.07 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1) to obtain a mixture of 7-iodo-4-methylisoindolinone and 7-iodoisoindolinone (44.8 mg, ratio 10/1, yield 50%).

Workup

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

Sources & evidence

ORD record
ord-67c101f9644c4906b0a4a7cbf1725fa0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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