Dimethylformamide → 2-Chloroquinoline-6-carbonitrile

HRID 1465732Notes

Reaction equation

HRID 1465732 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[CH:6]=[CH:5]2.[C:13]([Cu])#[N:14].CN(C=O)C>C(Cl)Cl>[Cl:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:13]#[N:14])[CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 128940866-Bromo-2-chloroquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 112524682-Chloroquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a flask containing a stir bar was added 6-bromo-2-chloroquinoline (0.90 g, 3.7 mmol), CuCN (0.50 g, 5.6 mmol) followed by addition of DMF (10 mL). The resulting mixture was then refluxed at 150° C. overnight. When the reaction appeared complete by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered, redissolved in DCM, absorbed onto silica gel, and purified by flash chromatography to provide the title product.

Workup

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationwhich was filtered
  4. dissolutionredissolved in DCM
  5. customabsorbed onto silica gel
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-dc14baba0b65476ea1ff72e5e90a17ee
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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