Potassium Cyanide → HCID 14280881, compound

HRID 868095Notes

Reaction equation

HRID 868095 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 10.2%

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 0.28 g of the title compound, mp 205°-207° C. The 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

Sources & evidence

ORD record
ord-28983e94af404b37afd34ec5662c3cc6
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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