Potassium Cyanide → HCID 54369126, compound

HRID 1416666Notes

Reaction equation

HRID 1416666 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:26])[C:17](Br)=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:27])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[C-:28]#[N:29].[K+]>CN1CCCC1=O.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:21]=[C:20]3[C:15]([C:16](=[O:26])[C:17]([C:28]#[N:29])=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:27])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 54184428HCID 54184428, compound

Product 1

HCID 54369126HCID 54369126, compoundYield 94.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
202.5 °C

Procedure

A mixture of 4-(3-bromo-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-piperazine-1-carboxylic acid ethyl ester (11.0 g, 25.1 mmol), Cul (5.3 g, 27.6 mmol) and KCN (1.8 g, 27.6 mmol) in 110 mL of 1-methyl-2-pyrrolidinone (NMP) was heated at 200-205° C. for 16 hours. On cooling to room temperature, the reaction mixture was diluted with chloroform (250 ml) upon which a thick precipitate formed. The mixture was filtered over celite (2×) and the clear brown organic filtrate was washed with water/brine (2×), dried (Na2SO4), filtered and concentrated in vacuo to a black oil. An off-white solid precipitated out by addition of hexane (150 ml) and ethyl acetate (300 ml). The solid was dissolved in chloroform, and activated charcoal and celite were added. The mixture was then filtered over celite. Evaporation of the solvent gave a white solid which was suspended in hot ethyl acetate and filtration afforded 9.1 g (94%) of 4-(3-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-piperazine-1-carboxylic acid ethyl ester as a white solid.

Workup

  1. temperatureOn cooling to room temperature
  2. customformed
  3. filtrationThe mixture was filtered over celite (2×)
  4. washthe clear brown organic filtrate was washed with water/brine (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a black oil
  8. customAn off-white solid precipitated out by addition of hexane (150 ml) and ethyl acetate (300 ml)
  9. dissolutionThe solid was dissolved in chloroform
  10. additionactivated charcoal and celite were added
  11. filtrationThe mixture was then filtered over celite
  12. customEvaporation of the solvent
  13. customgave a white solid which
  14. filtrationfiltration

Sources & evidence

ORD record
ord-88582347884f42fcbd50328cb25555a0
Source dataset
uspto-grants-1999_06
Patent number
US05914401

Reaction notes

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