Water → HCID 54363368, compound

HRID 1077702Notes

Reaction equation

HRID 1077702 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@H:16]1[F:18].O.S(=O)(=O)(O)O>C(O)(=O)C>[F:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 67771319HCID 67771319, compound

Product 1

HCID 54363368HCID 54363368, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.35 g (3.9 mmol) of ethyl 5,6,7,8-tetrafluoro-1-(trans-2-fluoro-cyclopropyl)-1,4-dihydro-4-oxo-3quinolinecarboxylate are heated under reflux for 2 hours in a mixture of 6.3 ml of acetic acid, 4.2 ml of water and 0.64 ml of concentrated sulphuric acid. After having been cooled down, this mixture is introduced into 40 ml of ice water and the undissolved precipitate is filtered off, washed with water and dried at 110° C. under high vacuum. Yield: 0.9 g (72% of theory) of 5,6,7,8-tetrafluoro-1-(trans-2-fluoro-cyclopropyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting point: 184°-186° C. (with decomposition). 5,6,7,8-Tetrafluoro-1-(cis-2-fluoro-cyclopropyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid is prepared in an analogous manner.

Workup

  1. temperatureAfter having been cooled down
  2. filtrationthe undissolved precipitate is filtered off
  3. washwashed with water
  4. customdried at 110° C. under high vacuum

Sources & evidence

ORD record
ord-8dc7983e45034680b1afc43b7f22aa9a
Source dataset
uspto-grants-1996_08
Patent number
US05545642

Reaction notes

Loading…