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

HRID 1290735Notes

Reaction equation

HRID 1290735 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:33])=[C:10]([N:14]3[CH2:18][CH2:17][CH:16]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][C:26]([NH:29]C(=O)C)=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2].Cl.[OH-].[Na+]>C(O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:33])=[C:10]([N:14]3[CH2:18][CH2:17][CH:16]([NH:19][S:20]([C:23]4[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=4)(=[O:22])=[O:21])[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:34])[C:5]([C:35]([OH:37])=[O:36])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 189182031-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(4-acetamidobenzenesulfonamido)-1-pyrrolidinyl]-3-quinolinecarboxylic acid

Product 1

HCID 189182091-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(4-aminobenzenesulfonamido)-1-pyrrolidinyl]-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the compound obtained in Example 14 is added a mixture solution made up of 100 ml of 2N hydrochloric acid and 10 ml of ethanol, and the resulting mixture is refluxed for 4 hours while heating. After cooling, the reaction mixture is neutralized with 2N sodium hydroxide solution and concentrated under reduced pressure. The residue is added to water which is then adjusted to pH 13 with 2N sodium hydroxide solution to dissolve, and any undissolved matter, if present, is removed. The solution is adjusted to pH 7 with acetic acid. Precipitating crystals are collected by filtration and washed. To the washed crystals is added water, pH adjusted to 3 to dissolve, and any undissolved matter, if present, is removed. The solution is then adjusted to pH 7 with 2N sodium hydroxide solution and precipitating crystals are collected by filtration and washed with water. Recrystallization from DMF-methanol gives 1.07 g of the titled compound. Melting point 214°-216° C.

Workup

  1. temperaturethe resulting mixture is refluxed for 4 hours
  2. temperaturewhile heating
  3. temperatureAfter cooling
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue is added to water which
  6. dissolutionto dissolve
  7. customany undissolved matter, if present, is removed
  8. customPrecipitating crystals
  9. filtrationare collected by filtration
  10. washwashed
  11. additionTo the washed crystals is added water
  12. dissolutionto dissolve
  13. customany undissolved matter, if present, is removed
  14. customprecipitating crystals
  15. filtrationare collected by filtration
  16. washwashed with water
  17. customRecrystallization from DMF-methanol

Sources & evidence

ORD record
ord-28aefd192dec4f92be9f004da9d82e1b
Source dataset
uspto-grants-1998_05
Patent number
US05753658

Reaction notes

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