7-bromo-N,N-dipropylisoquinolin-1-amine → 1-(Dipropylamino)isoquinoline-7-carbonitrile

HRID 14260

Reaction equation

HRID 14260 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[C:19]([Cu])#[N:20]>CN(C)C=O.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([C:19]#[N:20])[CH:11]=2)[CH:6]=[CH:7][N:8]=1)[CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 210859987-bromo-N,N-dipropylisoquinolin-1-amineHCID 178418546HCID 178418546, compound

Product 1

HCID 210851971-(Dipropylamino)isoquinoline-7-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-bromo-N,N-dipropylisoquinolin-1-amine (350 mg, 1.1 mmol) and CuCN (204 mg, 2.2 mmol) in N,N-dimethylformamide (2 mL) was stirred at reflux for 24 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate (3×50 mL). The combined organics were washed with saturated sodium chloride, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to provide 1-(dipropylamino)isoquinoline-7-carbonitrile (279 mg, which was used without any further characterization.

Workup

  1. temperatureat reflux for 24 h
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organics were washed with saturated sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b3881acd748434d9adb4b9528b554be
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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