Sodium Cyanide → Isoquinoline-5-carbonitrile

HRID 650209Notes

Reaction equation

HRID 650209 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.N([O-])=O.[Na+].C(=O)(O)[O-].[Na+].[I-].[C-]#N.[Na+].[Cu](C#N)[C:26]#[N:27]>Cl.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:26]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)#[N:27]

Participants

11

Reactant 6

HCID 8929Sodium CyanideHCID 30165Iodide IonHCID 707665-AminoisoquinolineHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 178418260HCID 178418260, compound

Product 1

HCID 459770Isoquinoline-5-carbonitrileYield 56%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) solution of 10.0 g (61.4 mol) of 5-aminoisoquinoline in 288 mL of 1.5N hydrochloric acid, was added 15 mL of 5.2M sodium nitrite in water. After approximately 5 minutes, a cool saturated solution of sodium bicarbonate was added to the reaction mixture until the reaction solution tested negative using the iodide and starch paper test. The resultant solution was poured into a cold (0-5° C.) biphasic mixture containing 300 ml of toluene and 150 mL of an aqueous solution containing 8.4 g (177 mmol) of sodium cyanide and 7.6 g (85 mmol) of copper cyanide. The resultant reaction mixture was warmed to room temperature, reacted for approximately 1 hour, and then diluted with a mixture of ethyl acetate and water. The resulting layers were separated, and the organic phase was dried over sodium sulfate, filtered, and then reduced to dryness under reduced pressure to provide 5.9 g of a yellow solid.

Workup

  1. customThe resultant reaction mixture
  2. customreacted for approximately 1 hour
  3. customThe resulting layers were separated
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-639b7ab56e404594a6a4561887f48501
Source dataset
uspto-grants-2001_08
Patent number
US06271235B1

Reaction notes

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