Dimethylformamide → 3-Chloroquinoline-7-carbonitrile

HRID 1465739Notes

Reaction equation

HRID 1465739 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([Cl:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:13]([Cu])#[N:14].CN(C=O)C>C(Cl)Cl>[Cl:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:13]#[N:14])[CH:11]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 533932407-Bromo-3-chloroquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 895252713-Chloroquinoline-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a flask containing a stir bar was added 7-Bromo-3-chloroquinoline (1.0 g, 4.1 mmol), CuCN (0.55 g, 6.2 mmol), and DMF (25 mL). The mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced 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 off. The crude product was adsorbed onto silica gel and purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product.

Workup

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationwhich was filtered off
  4. custompurified by silica gel column chromatography (Hexanes:DCM→1:1)

Sources & evidence

ORD record
ord-4e4be921e4394c1eb71db861ed04959f
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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