Chloroform → 7-Cyano-5-nitroindole

HRID 2086041Notes

Reaction equation

HRID 2086041 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[C:14]([Cu])#[N:15].[C-]#N.[K+].C(Cl)(Cl)Cl>CN(C=O)C.CCOC(C)=O>[C:14]([C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2)#[N:15]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 9032Potassium CyanideHCID 38603267-bromo-5-nitro-1H-indoleHCID 178418546HCID 178418546, compound

Product 1

HCID 154534677-Cyano-5-nitroindoleYield 78.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-bromo-5-nitroindole (2.5 g, 10.4 mmol), CuCN (3.0 g, 33.3 mmol) and KCN (3.0 g, 46.1 mmol) in 20 mL of DMF was stirred at 120° C. for 24 h. The reaction mixture was diluted with 500 mL of EtOAc and washed with brine several times. Organic layer was dried over Na2SO4 and concentrated in vacuo, yielding a brown oily residue which was subjected to column chromatography (CHCl3, neat) to provide 1.5 g (8.2 mmol, 77%) of the desired product.

Workup

  1. washwashed with brine several times
  2. dry with materialOrganic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customyielding a brown oily residue which

Sources & evidence

ORD record
ord-4f366a2464b04d72933db2a3934ec387
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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