Sodium Hydroxide → HCID 14071844, compound

HRID 358865Notes

Reaction equation

HRID 358865 reaction equation
B(F)(F)F.[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:26])=[C:14]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[C:15]=2[O:17][CH3:18])[C:10](=[O:27])[C:9]([C:28]([OH:30])=[O:29])=[CH:8]1)[CH3:6].[OH-].[Na+]>O>[CH2:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:26])=[C:14]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[C:15]=2[O:17][CH3:18])[C:10](=[O:27])[C:9]([C:28]([OH:30])=[O:29])=[CH:8]1)[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14071845HCID 14071845, compound

Product 1

HCID 14071844HCID 14071844, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

130 mg (0.0003 mole) of 1-ethyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid boron trifluoride addition product (prepared as described in Example 39) were dissolved in 30 ml of water. 0.36 ml of a 1N aqueous solution of sodium hydroxide was added to the solution, and the reaction mixture was concentrated by evaporation under reduced pressure to give crystals. These were recrystallized from ethanol and then washed with cold water, to give 70 mg of 1-ethyl-6-fluoro-8-methoxy-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a pale brown powder melting at 207°-209° C. (with decomposition).

Workup

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. customto give crystals
  3. customThese were recrystallized from ethanol
  4. washwashed with cold water

Sources & evidence

ORD record
ord-57cbfd5a3d2743a58e6f629df24d4c2d
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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