Trimethylsilyl cyanide → HCID 23084561, compound

HRID 2111642Notes

Reaction equation

HRID 2111642 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH:13]=[N:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH:3]=1.[C:22]([Si](C)(C)C)#[N:23]>C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>[CH3:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][C:11]=1[CH3:12])[C:6](=[O:8])[N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[CH:13]2[C:22]#[N:23]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 68916985HCID 68916985, compound

Product 1

HCID 23084561HCID 23084561, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 241BenzeneSolvent

Procedure

The product of above-mentioned (25-b) (0.45 g, 1.6 mmol), cyanotrimethylsilane (0.40 ml, 3.2 mmol) and aluminum chloride (13 mg) were stirred in anhydrous benzene (5.5 ml) at 25° C. for 20 hrs under an argon atmosphere. The reaction solution was concentrated under reduced pressure, and the residue was washed with petroleum ether to give 0.35 g of 5,6-dimethyl-2-(3-fluorophenyl)-3-cyano-isoindolin-1-one. [IUPAC name: 2-(3-fluorophenyl)-5,6-dimethyl-3-oxo-1-isoindolinecarbonitrile].

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washthe residue was washed with petroleum ether

Sources & evidence

ORD record
ord-490f5348cfb848b0a2cb20a4b7f237f4
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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