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

HRID 465374Notes

Reaction equation

HRID 465374 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([C:27]([O:29]CC)=[O:28])=[CH:20][N:21]3[CH:24]3[CH2:26][CH2:25]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[CH:23]=[C:22]3[C:17]([C:18](=[O:32])[C:19]([C:27]([OH:29])=[O:28])=[CH:20][N:21]3[CH:24]3[CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:33])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15021537Ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6-fluoro1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 679157567-(3-Pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 7-(1-t-butoxycarbonyl-3-pyrrolidinyloxy)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3carboxylate (210 mg) was dissolved in a mixture consisting of 0.7 ml of concentrated hydrochloric acid and 2.8 ml of acetic acid. The resulting solution was heated under reflux for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was recrystallized from ethanol, whereby 60 mg of the title compound was obtained as crystals.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7677fad717f24058a18f08e23d6b4e87
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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