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

HRID 580586Notes

Reaction equation

HRID 580586 reaction equation
C(OC([NH:8][C@H:9]1[C@@H: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]>C(O)C>[ClH:34].[NH2:8][C@H:9]1[C@@H: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 703540497-(cis-3-t-Butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 703535387-(cis-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 702EthanolSolvent

Procedure

A mixture of 7-(cis-3-t-butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.3 g) in ethanol (5 ml) and ethanolic hydrochloride (6 ml) was stirred for 2 hours at room temperature and then concentrated. To the residue was added ethanol and the resulting precipitate was collected by filtration and washed with ethanol to give the title compound (0.21 g) as pale yellowish powder, mp 274°-275° C. (decompd.).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added ethanol
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-7b06696456564b458965f004614d4990
Source dataset
uspto-grants-1988_06
Patent number
US04753953

Reaction notes

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