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

HRID 36713Notes

Reaction equation

HRID 36713 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-4c5dab8c559f41779f190a5fae0e566e
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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