Dimethylformamide → 3-Chloro-8-methyl-7-isoquinolinecarbonitrile

HRID 1465752Notes

Reaction equation

Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([Cl:13])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:14]([Cu])#[N:15].CN(C=O)C>C(Cl)Cl>[Cl:13][C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:14]#[N:15])[C:11]=2[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

To a flask containing a stir bar was added 7-Bromo-3-chloro-8-methylisoquinoline (0.63 g, 2.4 mmol), CuCN (0.33 g, 3.7 mmol), and DMF (10 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 mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered, re-dissolved in DCM, adsorbed into silica gel and purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product. LC/MS (IE, m/z): [M+1]+=203.

Workup

additionTo a flask containing a stir bar
temperaturecooled to room temperature
filtrationwhich was filtered
dissolutionre-dissolved in DCM
custompurified by silica gel column chromatography (Hexanes:DCM→1:1)

Sources & evidence

ORD record: ord-2e0606a46f114ebdac504b4c04d771bc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999991B2

Reaction notes

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