Formaldehyde → 7-(3,4-Dimethyl-1-piperazinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxlic acid

HRID 370715Notes

Reaction equation

HRID 370715 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:21])=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH:16]([CH3:20])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4]1)[CH3:2].[CH2:26]=O>C(O)=O>[CH3:20][CH:16]1[N:17]([CH3:26])[CH2:18][CH2:19][N:14]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:22])[C:5]([C:23]([OH:25])=[O:24])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:21])[CH2:15]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 3948Lomefloxacin

Product 1

HCID 134776637-(3,4-Dimethyl-1-piperazinyl)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxlic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1.40 g of 1-ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid, 2.8 ml of 90% formic acid and 2.2 ml of 37% formalin was heated for 4 hours under reflux. The reaction mixture was evaporated and the residue was dissolved in water. The solution was neutralized with aqueous sodium bicarbonate. The precipitate was filtered and recrystallized from ethanol to give 0.32 g of the title compound as colorless needles, M.p. 211.5°-212° C.

Workup

  1. temperaturewas heated for 4 hours
  2. temperatureunder reflux
  3. customThe reaction mixture was evaporated
  4. dissolutionthe residue was dissolved in water
  5. filtrationThe precipitate was filtered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-841b7245c77b43c88fd1851b8beb19af
Source dataset
uspto-grants-1985_07
Patent number
US04528287

Reaction notes

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