Ethyl 8-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate → 1-Cyclopropyl-1,4-dihydro-7-fluoro-8-chloro-4-oxo-quinoline-3-carboxylic Acid

HRID 2269209Notes

Reaction equation

HRID 2269209 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([Cl:18])[C:11]([F:17])=[CH:12][CH:13]=2)[N:8]([CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)=[O:5])C>C(O)(=O)C.O.S(=O)(=O)(O)O>[CH:19]1([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([F:17])[C:10]=3[Cl:18])[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]2)[CH2:20][CH2:21]1

Participants

5

Reactant 1

HCID 18333191Ethyl 8-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 183332011-Cyclopropyl-1,4-dihydro-7-fluoro-8-chloro-4-oxo-quinoline-3-carboxylic Acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A quantity of 1.93 g of ethyl-1-cyclopropyl-1,4-dihydro-7-fluoro-8-chloro-4-oxo-quinoline-3-carboxylate is dissolved in 30 ml of a mixture of acetic acid, water and sulfuric acid (8/6/1). the mixture is refluxed for 3 hours and cooled to room temperature. The desired compound is collected by filtration and air dried.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. filtrationThe desired compound is collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-2de10544f14043b88964dee4ad89569d
Source dataset
uspto-grants-2001_12
Patent number
US06329391B1

Reaction notes

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