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Methane → 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(4-acetamidobenzenesulfonamido)-1-pyrrolidinyl]-3-quinolinecarboxylic acid

HRID 1290734
Notes
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Reaction equation

HRID 1290734 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2].[C:25]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)(=[O:27])[CH3:26].C>N1C=CC=CC=1.C1C=CC=CC=1.CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:18][CH2:17][CH:16]([NH:19][S:35]([C:32]4[CH:31]=[CH:30][C:29]([NH:28][C:25](=[O:27])[CH3:26])=[CH:34][CH:33]=4)(=[O:37])=[O:36])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 297MethaneHCID 8481N-Acetylsulfanilyl chlorideHCID 11724607HCID 11724607, compound

Product 1

HCID 189182031-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(4-acetamidobenzenesulfonamido)-1-pyrrolidinyl]-3-quinolinecarboxylic acidYield 32.7%

Reagents, catalysts & solvents 3

HCID 241Benzene
Solvent
HCID 1049PyridineSolvent
HCID 6228DimethylformamideSolvent

Procedure

2.80 g of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-amino-1-pyrrolidinyl)-3-quinolinecarboxylic acid (see REFERENCE SYNTHESIS EXAMPLE hereinafter) is suspended in 100 ml of pyridine. To this is slowly added 3.88 g of 4-acetamidobenzenesulfonyl chloride in 20 ml of benzene. The mixture is stirred for 1 hour under ice-cooling and then overnight at room temperature. After evaporating off the solvent from the reaction mixture, the residue is added water and then adjusted to pH 12 with 2N sodium hydroxide solution. Any undissolved matter, if present, is filtered off. The filtrate is adjusted to pH 7 with acetic acid. The precipitated crystals are collected by filtration and washed. The crystals are then suspended in 100 ml of water. The suspension is adjusted to pH 4 with acetic acid, stirred and then filtered to recover the crystals, which are then thoroughly washed with water. The crude crystals thus obtained are dissolved in dimethylformamide (DMF), treated with activated charcoal, and recrystallized from DMF-methanol to give 1.45 g of the titled compound.

Workup

  1. temperaturecooling
  2. customovernight
  3. customat room temperature
  4. customAfter evaporating off the solvent from the reaction mixture
  5. additionthe residue is added water
  6. filtrationAny undissolved matter, if present, is filtered off
  7. filtrationThe precipitated crystals are collected by filtration
  8. washwashed
  9. stirringstirred
  10. filtrationfiltered
  11. customto recover the crystals, which
  12. washare then thoroughly washed with water
  13. customThe crude crystals thus obtained
  14. customrecrystallized from DMF-methanol

Sources & evidence

ORD record
ord-00ecf782a6eb4c62b73d4b91c84051fe
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753658

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes