Iodine → 7-Iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinone

HRID 21102Notes

Reaction equation

HRID 21102 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:21].[K+].II.[N:25]([O:27]C(C)(C)C)=[O:26]>C(#N)C.[Cu](I)I>[I:21][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[C:16]([N+:25]([O-:27])=[O:26])[C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 10906Tert-Butyl nitriteHCID 684876617-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone

Product 1

HCID 684887357-Iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinoneYield 31.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone (202 mg, 0.747 mmol) was dissolved in acetonitrile (10.1 mL), and the solution was treated with potassium iodide (149 mg, 0.896 mmol), copper iodide (171 mg, 0.896 mmol), iodine (228 mg, 0.896 mmol) and tert-butyl nitrite (0.266 mL, 0.896 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1) to obtain 7-iodo-4-(4-hydroxy-3-methoxy-5-nitrophenyl)isoindolinone (100 mg, yield 31%).

Workup

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=15/1)

Sources & evidence

ORD record
ord-bdbbee7acee84f529f217d38b8790b81
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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