Potassium Cyanide → HCID 14280881, compound

HRID 980698Notes

Reaction equation

HRID 980698 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11](N)=[C:12]([F:16])[CH:13]=2)[N:8]([CH2:18][CH3:19])[CH:7]=1)=[O:5])[CH3:2].N([O-])=O.[Na+].[C-:24]#[N:25].[K+].[OH-].[NH4+]>Cl.O>[CH2:1]([O:3][C:4]([C:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([C:24]#[N:25])=[C:12]([F:16])[CH:13]=2)[N:8]([CH2:18][CH3:19])[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 54234399HCID 54234399, compound

Product 1

HCID 14280881HCID 14280881, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 2.78 g (10 mmole) of 7-amino-1,4-dihydro-1-ethyl-6-fluoro-3-quinolinecarboxylic acid ethyl ester in 40 ml of 1N HCl at 8° was added a solution of 0.72 g (10.5 mml) of sodium nitrite and 5 ml of water portionwise keeping the temperature at 8° C. The orange solution was stirred at 5° to 8° C. for 0.5 hours. To a solution of 1.07 g (12 mmol) of cuprous cyanide, 2.28 g (35 mmol) of potassium cyanide and 25 ml of water at 45°-50° C. was added the diazonium solution over 10 minutes. The foaming mixture was heated with stirring at 50°-60° C. for 1.25 hours, then treated with 10 ml of 29% ammonium hydroxide and stirred at 50° C. for 20 minutes. The solution was cooled with ice and the solid collected by filtration. The solid was recrystallized from acetonitrile to give acetonitrile filtrate was evaporated to dryness and the residue was triturated with ethers to yield an additional 0.63 g of product.

Workup

  1. customat 8° C
  2. temperatureThe foaming mixture was heated
  3. stirringwith stirring at 50°-60° C. for 1.25 hours
  4. stirringstirred at 50° C. for 20 minutes
  5. temperatureThe solution was cooled with ice
  6. filtrationthe solid collected by filtration
  7. customThe solid was recrystallized from acetonitrile
  8. customto give acetonitrile filtrate
  9. customwas evaporated to dryness
  10. customthe residue was triturated with ethers

Sources & evidence

ORD record
ord-9476398995d443b2bd0cdf07f9ff6149
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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