Dimethylformamide → Isoquinoline-5-carbonitrile

HRID 1051238Notes

Reaction equation

HRID 1051238 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[CH3:12][N:13](C)C=O>C(OCC)(=O)C.[C-]#N.[C-]#N.[Zn+2]>[CH:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([C:12]#[N:13])[C:3]=2[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 7364875-Bromoisoquinoline

Product 1

HCID 459770Isoquinoline-5-carbonitrileYield 97%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromoisoquinoline (8 g, 38.65 mmol) and dimethyl formamide (100 mL) were mixed and stirred. The reaction solution was added with Zn(CN)2 (2.72 g, 23.19 mmol) and Ph(PPH)4 (1.78 g, 1.55 mmol), followed by stirring for about 4 hours at 100° C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (5.8 g, 97%).

Workup

  1. stirringby stirring for about 4 hours at 100° C
  2. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea71c73fbb2d47259f95ea229eaba789
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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