Formic Acid → N-Methyl Gatifloxacin HCl

HRID 358862

Reaction equation

HRID 358862 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:21][CH2:20][NH:19][CH:18]([CH3:22])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[ClH:28].[CH:29](O)=O>C=O>[ClH:28].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:21][CH2:20][N:19]([CH3:29])[CH:18]([CH3:22])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 313Hydrochloric Acid2×HCID 5379Gatifloxacin

Product 1

HCID 67925406N-Methyl Gatifloxacin HCl

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 1.5 g (0.004 mole) of 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (free form) (prepared as described in Example 22, but omitting the final reaction with hydrochloric acid) in a mixture of 75 ml of 90% aqueous formic acid and 45 ml of 37% aqueous formaldehyde was heated under reflux for 15 hours. 8 ml of concentrated hydrochloric acid were then added to the reaction mixture, and the solvent (formic acid, formalin and water) was then removed by evaporation under reduced pressure. Methanol was then added to the residue, and the resulting solution was filtered to remove insoluble material. The filtrate was evaporated to dryness under reduced pressure, and the residue was washed with ethanol to afford 1.35 g of 1-cyclopropyl-6-fluoro-8-methoxy-7-(3,4-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a colorless powder melting at 218°-221° C. (with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customthe solvent (formic acid, formalin and water) was then removed by evaporation under reduced pressure
  4. additionMethanol was then added to the residue
  5. filtrationthe resulting solution was filtered
  6. customto remove insoluble material
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. washthe residue was washed with ethanol

Sources & evidence

ORD record
ord-95c0d2d441694e68a2d01dbdeeb29b40
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Linked notes

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