Sodium Methoxide → HCID 18918207, compound

HRID 1290733Notes

Reaction equation

HRID 1290733 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:33])=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH2:16][CH2:15]3)[C:11]=2F)[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2].[CH3:38][O-:39].[Na+]>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:33])=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:27][CH:28]=4)(=[O:22])=[O:21])[CH2:16][CH2:15]3)[C:11]=2[O:39][CH3:38])[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18918200HCID 18918200, compound

Product 1

HCID 18918207HCID 18918207, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.16 g of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(4-acetamidobenzenesulfonyl)-1-piperazinyl]-3-quinolinecarboxylic acid obtained in Example 1 is dissolved in 100 ml of dimethylformamide (DMF). To this is added 7.72 g of 28% sodium methylate and the mixture is refluxed for 2 hours while heating. Then, the reaction mixture is concentrated under reduced pressure. To the residue is added water to dissolve and the solution is neutralized with 2N hydrochloric acid. The precipitated crystals are collected by filtration to give 2.0 g of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(4-acetamidobenzenesulfonyl)-1-piperazinyl]-8-methoxy-3-quinolinecarboxylic acid. This is suspended in 2N sodium hydroxide solution, and the suspension is refluxed for 2 hours while stirring. The reaction mixture is adjusted to pH 7.0 with acetic acid. The precipitated crystals are collected by filtration and washed with water to give 1.22 g of the titled compound. Melting point: 145° C. (decomp.)

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperaturewhile heating
  3. concentrationThen, the reaction mixture is concentrated under reduced pressure
  4. additionTo the residue is added water
  5. dissolutionto dissolve
  6. filtrationThe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-ae49b76f26e647bf8f724655aec4c3cf
Source dataset
uspto-grants-1998_05
Patent number
US05753658

Reaction notes

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