Water → HCID 13337934, compound

HRID 1284526Notes

Reaction equation

HRID 1284526 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].O>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][N:17]([CH2:27][CH2:26][C:25]([O:29][CH3:30])=[O:28])[CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 2764CiprofloxacinHCID 7294Methyl Acrylate

Product 1

HCID 13337934HCID 13337934, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.31 g (0.01 mole) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid and 5 g (0.058 mole) of methyl acrylate in 50 ml of ethanol is heated under reflux for 2 hours. The solution is poured into 10 ml of water and the precipitate is filtered off with suction, washed with methanol and recrystallized from glycol monomethyl ether. 2.9 g (70% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-methoxycarbonylethyl)-1-piperazinyl]-3-quinolinecarboxylic acid of decomposition point 192° to 194° C. are obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. filtrationthe precipitate is filtered off with suction
  4. washwashed with methanol
  5. customrecrystallized from glycol monomethyl ether

Sources & evidence

ORD record
ord-bb3067b4f9ba4cf79dd58852c16ed7e2
Source dataset
uspto-grants-1986_01
Patent number
US04563448

Reaction notes

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