Indole-5-carbonitrile → HCID 59318394, compound

HRID 423348Notes

Reaction equation

HRID 423348 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[Cl:12]N1C(=O)CCC1=O>CN(C=O)C>[Cl:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 27513Indole-5-carbonitrileHCID 31398Chlorosuccinimide

Product 1

HCID 59318394HCID 59318394, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-cyanoindole (3.0 g, 21 mmol) in dry DMF (50 ml) was added N-chlorosuccinimide (2.94 g, 22 mmol) and the solution stirred at room temperature for 1 hour. The solution was left standing over the weekend. LC/MS showed a single product. Added ethyl acetate (150 ml) and diethyl ether (50 ml) and washed with water (3×300 ml). Dried over MgSO4 and evaporated off the solvent to yield 3.9 g of the title compound as a pale yellow solid. δH (400 MHz, d6-DMSO) 7.54 (1H, dd), 7.61 (1H, dd), 7.78 (1H, d), 8.01-8.02 (1H, m), 12.2 (1H, broad s). MS (from LCMS of reaction mixture) (ES):C9H5ClN2 requires 176; found 177 (MH+).

Workup

  1. waitThe solution was left
  2. washAdded ethyl acetate (150 ml) and diethyl ether (50 ml) and washed with water (3×300 ml)
  3. dry with materialDried over MgSO4
  4. customevaporated off the solvent

Sources & evidence

ORD record
ord-b5aacc7bf9824c8e992a442191a3c503
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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