Water → HCID 23084610, compound

HRID 1783303Notes

Reaction equation

HRID 1783303 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.[C:9]([C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])(=O)[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.O>CN(C)C=O>[N:13]1[CH:14]=[CH:15][C:10]([C:9]2[C:17]3[C:18](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:19](=[O:20])[O:21][CH:22]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23084873HCID 23084873, compound

Product 1

HCID 23084610HCID 23084610, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (purity 60%, 2.0 g) was suspended in dimethylformamide (100 mL), and trimethylsulfoxonium iodide (11 g) was added, and the mixture was stirred at room temperature for 1 hr. Then, methyl 2-isonicotinoylbenzoate (11 g) was added, and the mixture was further stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration to give 4-(pyridin-4-yl)isocoumarin (4.9 g).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-2a6b477751c442beb270a365d9549d41
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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