Water → 5,7-Dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 981133Notes

Reaction equation

HRID 981133 reaction equation
[Cl:1][C:2]1[C:11]([F:12])=[C:10]([Cl:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:17]([O:19]CC)=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.O.S(=O)(=O)(O)O>C(O)(=O)C>[Cl:1][C:2]1[C:11]([F:12])=[C:10]([Cl:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 15070039Ethyl 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 150700405,7-Dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 100.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.2 g of ethyl 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are heated under reflux in a mixture of 38 ml of acetic acid, 30 ml of water and 4.3 ml of concentrated sulphuric acid for 2.5 hours. After cooling, the mixture is poured into 250 ml of ice-water and the precipitate is filtered off with suction, washed with water and dried. 4.8 g of 5,7-dichloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 277°-278° C. are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-19c126f256274b3abaf672c3b219e2dc
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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