Sulfuric Acid → 1-Cyclopropyl-7-(4-hydroxy-1-piperidyl)-6-fluoro-8-methyl-1,4dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1722302Notes

Reaction equation

HRID 1722302 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[B+3].[Na+].[OH-].[OH-].[OH-].S(=O)(=O)(O)O>[OH-].[Na+]>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]4)[C:12]=3[CH3:14])[C:7](=[O:23])[C:6]([C:24]([OH:26])=[O:25])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15622512HCID 15622512, compoundHCID 178419133HCID 178419133, compound

Product 1

HCID 101331361-Cyclopropyl-7-(4-hydroxy-1-piperidyl)-6-fluoro-8-methyl-1,4dihydro-4-oxoquinoline-3-carboxylic acidYield 63.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-Cyclopropyl-7-(4-oxo-1-piperidyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.25 g) is dissolved in 1% aqueous sodium hydroxide (28 ml), and thereto is added sodium boron hydroxide (0.1 g) at room temperature. The mixture is stirred at the same temperature for 30 minutes, and the resulting mixture is poured into ice water and then acidified with conc. sulfuric acid. The mixture is extracted with dichloromethane, and the solvent is distilled off. The resulting residue is crystallized by adding thereto ethyl acetate, and then recrystallized from chloroform-methanol to give 1-cyclopropyl-7-(4-hydroxy-1-piperidyl)-6-fluoro-8-methyl-1,4dihydro-4-oxoquinoline-3-carboxylic acid (0.16 g), as pale yellow crystals, m.p. 234°-236° C.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. distillationthe solvent is distilled off
  3. customThe resulting residue is crystallized
  4. additionby adding
  5. customethyl acetate, and then recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-d0fdbee5fa654b6f8cca936f013f0ea7
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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