Water → 1-Cyclopropyl-8-ethenyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 129407Notes

Reaction equation

HRID 129407 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[CH:14]=[CH2:15])[C:7](=[O:18])[C:6]([C:19]([O:21]CC)=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.O.S(=O)(=O)(O)O>C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11]([F:16])[C:12]=3[CH:14]=[CH2:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 19371459Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-vinyl-3-quinolinecarboxylate

Product 1

HCID 193650241-Cyclopropyl-8-ethenyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.9 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-vinyl-3-quinolinecarboxylate is refluxed for 4 hours in a mixture of 8 ml of glacial acetic acid, 0.6 ml of water and 0.2 ml of concentrated sulphuric acid. At reflux temperature, the reaction mixture is then treated with 10 ml of water. The solid is filtered off with suction at room temperature, washed with water and dried. 0.58 g of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-vinyl-3-quinolinecarboxylic acid (71% of theory) is obtained.

Workup

  1. temperatureAt reflux temperature
  2. filtrationThe solid is filtered off with suction at room temperature
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-793fbb69ae174f09b85f6e77e6a1a027
Source dataset
uspto-grants-1995_11
Patent number
US05468742

Reaction notes

Loading…