Chlorosuccinimide → HCID 13930512, compound

HRID 878992Notes

Reaction equation

HRID 878992 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.[Cl:12]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CO>[Cl:12][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 851461H-indole-6-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 13930512HCID 13930512, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-indole carbonitrile (1.0 g) in methanol (10 mL) was added N-chlorosuccinimide (1.2 g) at room temperature, and then the reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.3 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-041be5a76e344f248b4d7c0253d4f511
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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