Ciprofloxacin → 4-Quinolone-3-carboxylic acid

HRID 637947Notes

Reaction equation

HRID 637947 reaction equation
C1([N:4]2[C:13]3[C:8](=[CH:9][C:10](F)=[C:11](N4CCNCC4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)CC1.BrCC(OCC)=O.C(N(CC)CC)C.[I-].[K+]>CN(C)C=O.O>[O:21]=[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:4][CH:5]=[C:6]1[C:22]([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 2764CiprofloxacinHCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 2208754-Quinolone-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.3 g (0.01 mole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid in 50 ml of dimethylformamide are heated at 90° C. with 2.5 g (0.015 mole) of ethyl bromoacetate, 2.1 g (0.02 mole) of triethylamine and 2.5 g of potassium iodide for 5 hours. The reaction mixture is poured into 30 ml of water and the precipitate is filtered off with suction, washed with water and recrystallised from methanol. 2.5 g of 1-cyclopropyl-6-fluoro-7-[4-ethoxycarbonylmethyl)-1-piperazinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 192° to 194° C. are obtained.

Workup

  1. filtrationthe precipitate is filtered off with suction
  2. washwashed with water
  3. customrecrystallised from methanol

Sources & evidence

ORD record
ord-81f20c655dd645c8937797ee91b00226
Source dataset
uspto-grants-1985_12
Patent number
US04559342

Reaction notes

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