Hydrochloric Acid → 5-Amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 2291288Notes

Reaction equation

HRID 2291288 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:23]C(OCC)=O)[C:10]([F:22])=[C:11]([N:15]4[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:29])[C:6]([C:30]([O:32]CC)=[O:31])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].[ClH:37]>C(O)C>[ClH:37].[NH2:23][C:9]1[C:10]([F:22])=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH:17]([CH3:21])[CH2:16]2)[C:12]([F:14])=[C:13]2[C:8]=1[C:7](=[O:29])[C:6]([C:30]([OH:32])=[O:31])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21279709Ethyl 1-cyclopropyl-5-ethoxycarbonylamino-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 679476925-Amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 1-cyclopropyl-5-ethoxycarbonylamino-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate, 20% aqueous sodium hydroxide, and ethanol was refluxed for 12 hours. The reaction mixture was treated with activated carbon and adjusted at pH 1-2 with 10% hydrochloric acid. After cooling, the resulting crystals were collected by filtration and recrystallization from water-ethanol to give 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride, m.p. >300° C.

Workup

  1. temperaturewas refluxed for 12 hours
  2. additionThe reaction mixture was treated with activated carbon
  3. temperatureAfter cooling
  4. filtrationthe resulting crystals were collected by filtration and recrystallization from water-ethanol

Sources & evidence

ORD record
ord-09334dd78d5f4611a10516869370b268
Source dataset
uspto-grants-1989_01
Patent number
US04795751

Reaction notes

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