Water → 2-Pyridinesulfonic acid,2,3-dihydro-7-iodo-5-methoxy-1-oxo-1h-isoindol-4-yl ester

HRID 21300Notes

Reaction equation

HRID 21300 reaction equation
[OH:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:14].C(N(CC)CC)C.Cl.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30].O>C(#N)C>[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29]([O:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:14])(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13791306Pyridine-2-sulfonyl chloride hydrochlorideHCID 684899574-Hydroxy-5-methoxy-7-iodoisoindolinone

Product 1

HCID 768478832-Pyridinesulfonic acid,2,3-dihydro-7-iodo-5-methoxy-1-oxo-1h-isoindol-4-yl esterYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-5-methoxy-7-iodoisoindolinone (0.465 g, 1.52 mmol) was dissolved in acetonitrile (10.0 mL), and the solution was added with triethylamine (0.850 mL, 6.09 mmol) and 2-pyridinesulfonyl chloride hydrochloride (0.488 g, 2.28 mmol), followed by stirring at room temperature for 5 hours. The reaction mixture was added with water (8.0 mL) and stirred at room temperature for 30 minutes. The precipitated crystal was collected by filtration to obtain 4-(2-pyridinesulfonyloxy)-5-methoxy-7-iodoisoindolinone (0.468 g, yield 69%).

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-f69036e0c1b0458aa34d230debaab914
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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