Hydrochloric Acid → HCID 14422906, compound

HRID 1032010Notes

Reaction equation

HRID 1032010 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][N:9]2[CH:15]2[CH2:17][CH2:16]2)=[CH:4][C:3]=1[F:24].[C:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26].CC(C)([O-])C.[K+].Cl>O1CCOCC1>[C:25]([CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][N:9]2[CH:15]2[CH2:16][CH2:17]2)=[CH:4][C:3]=1[F:24])#[N:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 13885558HCID 13885558, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14422906HCID 14422906, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.0 g of ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-8-nitro-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 added in portions at room temperature. The mixture is stirred overnight and then heated to 50° for a further 4 hours. After cooling to room temperature, the mixture is diluted using ice-water and rendered acidic using HCl. The mixture is extracted using methylene chloride, and the organic phase is dried and concentrated. The residue is recrystallized from isopropanol.

Workup

  1. temperatureheated to 50° for a further 4 hours
  2. additionthe mixture is diluted
  3. extractionThe mixture is extracted
  4. customthe organic phase is dried
  5. concentrationconcentrated
  6. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-e9fd7094c0604c02bb4e59f98037e7bc
Source dataset
uspto-grants-1990_09
Patent number
US04956465

Reaction notes

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