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

HRID 1032014Notes

Reaction equation

HRID 1032014 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[N+:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])#[C-:24].CC(C)([O-])C.[K+].Cl>O.O1CCOCC1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N+:23]#[C-:24])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 533707Ethyl isocyanoacetateHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 22167259Ethyl 1-cyclopropyl-7-(ethoxycarbonyl-isocyanomethyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylateYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2.7 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate and 1.92 g of ethyl isocyanoacetate are initially introduced into 30 ml of dioxane. 1.91 g of potassium tert-butoxide are added and the mixture is heated to reflux for 3 hours. 0.39 g of potassium tert-butoxide is then added once more and the mixture is once more boiled for 2 hours. It is then diluted using water, acidified using HCl and the solid is isolated. After separation on silica gel (eluant CH2Cl2 /MeOH 95/5), 1.0 g of the title compound is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 3 hours
  3. additionIt is then diluted
  4. customthe solid is isolated
  5. customAfter separation on silica gel (eluant CH2Cl2 /MeOH 95/5)

Sources & evidence

ORD record
ord-0238a271edfe45d891535660d0c02662
Source dataset
uspto-grants-1990_09
Patent number
US04956465

Reaction notes

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