Hydrochloric Acid → 7-(3-Pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-8-methoxy-1,4--dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 465390Notes

Reaction equation

HRID 465390 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]([O:24][CH3:25])=[C:22]3[C:17]([C:18](=[O:32])[C:19]([C:29]([OH:31])=[O:30])=[CH:20][N:21]3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][C:15]=2[F:33])[CH2:9]1)=O)(C)(C)C.[ClH:34]>C(O)(=O)C>[ClH:34].[NH:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:23]([O:24][CH3:25])=[C:22]3[C:17]([C:18](=[O:32])[C:19]([C:29]([OH:31])=[O:30])=[CH:20][N:21]3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][C:15]=2[F:33])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 150215837-(1-t-Butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 679155817-(3-Pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-8-methoxy-1,4--dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The whole amount of the 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid obtained above was dissolved in a mixture which consisted of 1.25 ml of concentrated hydrochloric acid and 5 ml of acetic acid. The resultant solution was heated under reflux for 1 hour. The reaction mixture was concentrated to dryness under reduced pressure. The residue thus obtained was recrystallized from ethanol, whereby 120 mg of the title compound was obtained as colorless needle crystals.

Workup

  1. dissolutionabove was dissolved in a mixture which
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. customThe residue thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-7ffd9c3b19444d5e8d0f1d0392d9af59
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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