Hydrochloric Acid → 7-(3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride

HRID 580577Notes

Reaction equation

HRID 580577 reaction equation
C(OC([NH:8][CH:9]1[CH:13]([CH3:14])[CH2:12][N:11]([C:15]2[C:24]([F:25])=[C:23]3[C:18]([C:19](=[O:32])[C:20]([C:29]([OH:31])=[O:30])=[CH:21][N:22]3[CH:26]3[CH2:28][CH2:27]3)=[CH:17][C:16]=2[F:33])[CH2:10]1)=O)(C)(C)C.[ClH:34]>CO>[ClH:34].[NH2:8][CH:9]1[CH:13]([CH3:14])[CH2:12][N:11]([C:15]2[C:24]([F:25])=[C:23]3[C:18]([C:19](=[O:32])[C:20]([C:29]([OH:31])=[O:30])=[CH:21][N:22]3[CH:26]3[CH2:28][CH2:27]3)=[CH:17][C:16]=2[F:33])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 139331017-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 139205727-(3-Amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-(3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.27 g) was dissolved in a mixture of methanol (5 ml) and concentrated hydrochloric acid (5 ml) and stirred at room temperature for 30 minutes. After the reacting mixture was concentrated under reduced pressure, the resulting residue was dissolved in ethanol (10 ml) and crystallized with cooling. The resulting precipitate was recrystallized from methanol to give the title compound (0.14 g) as pale yellow powder, mp 272°-274° C.

Workup

  1. concentrationAfter the reacting mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ethanol (10 ml)
  3. customcrystallized
  4. temperaturewith cooling
  5. customThe resulting precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-e9e3f3ea12494c86975d71e914709420
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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