Hydrochloric Acid → Ethyl 8-cyano-7-(cyano-ethoxycarbonyl-methyl-)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

HRID 1032012Notes

Reaction equation

HRID 1032012 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8][N:9]2[CH:14]2[CH2:16][CH2:15]2)=[CH:4][C:3]=1[F:23].[C:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[N:25].CC(C)([O-])C.[K+].Cl>O1CCOCC1>[C:12]([C:11]1[C:2]([CH:26]([C:24]#[N:25])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:3]([F:23])[CH:4]=[C:5]2[C:10]=1[N:9]([CH:14]1[CH2:16][CH2:15]1)[CH:8]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]2=[O:22])#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 23431783Ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14422907Ethyl 8-cyano-7-(cyano-ethoxycarbonyl-methyl-)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.8 g of ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate and 1.92 g of ethyl cyanoacetate are initially introduced into 30 ml of dioxane. 1.91 g of potassium tert-butoxide are metered in at room temperature. The mixture is stirred overnight and then ice-water is added. It is rendered acidic using HCl and extracted using methylene chloride. The organic phase is dried and concentrated. The residue is stirred once more with water and the solid is isolated.

Workup

  1. customare metered in at room temperature
  2. extractionextracted
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. stirringThe residue is stirred once more with water
  6. customthe solid is isolated

Sources & evidence

ORD record
ord-db653b2c27d94beb849404635ded44ba
Source dataset
uspto-grants-1990_09
Patent number
US04956465

Reaction notes

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