Acetic Acid → 1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 637291Notes

Reaction equation

HRID 637291 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C(O)(=O)C.S(=O)(=O)(O)O>O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester

Product 1

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 103.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 94 g of ethyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (7), 600 ml of glacial acetic acid, 450 ml of water and 70 ml of concentrated sulphuric acid is heated under reflux for 1.5 hours. Thereafter, the hot suspension is poured onto ice, and the precipitate is filtered off under suction, rinsed thoroughly with water and dried in vacuo at 100° C. In this manner, 88.9 g of pure 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid II of melting point 228°-230° C. (decomposition) are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hours
  3. additionThereafter, the hot suspension is poured onto ice
  4. filtrationthe precipitate is filtered off under suction
  5. washrinsed thoroughly with water
  6. customdried in vacuo at 100° C

Sources & evidence

ORD record
ord-c911b13a4c2c40caa5834f0b4e5c847d
Source dataset
uspto-grants-1985_12
Patent number
US04556658

Reaction notes

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