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

HRID 280103Notes

Reaction equation

HRID 280103 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-oxo-3-quinolinecarboxylate, 600 ml of glacial acetic acid, 450 ml of water and 70 ml of concentrated sulphuric acid is heated to reflux for 1.5 hours. The hot suspension is then poured onto ice, and the precipitate is filtered off with suction, thoroughly washed 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-oxo-3-quinolinecarboxylic acid of melting point 228°-230° C. (decomposition) are obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1.5 hours
  3. additionThe hot suspension is then poured onto ice
  4. filtrationthe precipitate is filtered off with suction
  5. washthoroughly washed with water
  6. customdried in vacuo at 100° C

Sources & evidence

ORD record
ord-33e2208c45f4492b94b545f15e16c07a
Source dataset
uspto-grants-1986_05
Patent number
US04588726

Reaction notes

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