Hydrochloric Acid → 7-(5-Aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 1494815Notes

Reaction equation

HRID 1494815 reaction equation
C([NH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:15]1[CH:24]=[C:23]3[C:18]([C:19](=[O:31])[C:20]([C:28]([OH:30])=[O:29])=[CH:21][N:22]3[CH:25]3[CH2:27][CH2:26]3)=[CH:17][C:16]=1[F:32])[CH2:9]2)(=O)C.[ClH:33].O>C(O)C>[ClH:33].[NH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][N:10]([C:15]1[CH:24]=[C:23]3[C:18]([C:19](=[O:31])[C:20]([C:28]([OH:30])=[O:29])=[CH:21][N:22]3[CH:25]3[CH2:27][CH2:26]3)=[CH:17][C:16]=1[F:32])[CH2:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 572941317-(5-Acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 679224197-(5-Aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

304 mg of 7-(5-acetamidomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro--4-oxoquinoline-3-carboxylic acid was added to a mixed solution of 12 ml of concentrated HCl, 2.5 ml of water, and 5 ml of ethanol, and the mixture was heated under reflux for 15 hours. After cooling under atmosphere, the crystals deposited were collected by filtration and washed with ethanol to obtain 264 mg of 7-(5-aminomethyl-2-isoindolinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAfter cooling under atmosphere
  4. filtrationthe crystals deposited were collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-82f27b2c1e484418ab41453384d7a0ba
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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