Hydrochloric Acid → 1-Cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3 carboxylic acid

HRID 1584828Notes

Reaction equation

HRID 1584828 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:34])=[C:11]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[CH2:18]5)[C:12]=3[CH3:14])[C:7](=[O:35])[C:6]([C:36]([O:38]CC)=[O:37])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].O1CCOCC1.Cl>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:34])=[C:11]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[CH2:20][N:19]([S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])[CH2:18]5)[C:12]=3[CH3:14])[C:7](=[O:35])[C:6]([C:36]([OH:38])=[O:37])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 15870841HCID 15870841, compound

Product 1

HCID 158708471-Cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3 carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 3 ml of ethanol was suspended 0.30 g of ethyl 1-cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate, and 3 ml of 1N aqueous sodium hydroxide solution and 3 ml of dioxane were added to the suspension, after which the resulting mixture was stirred at room temperature for two hours. To the reaction mixture was added 3 ml of 1N hydrochloric acid, and the crystals thus formed were collected by filtration, to obtain 0.27 g of colorless, crystalline 1-cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. additionwere added to the suspension
  2. customthe crystals thus formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ea2d9c52cc254bc4a7fed8e1f85442ae
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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