HCID 70111644, compound → HCID 15458203, compound

HRID 377292Notes

Reaction equation

HRID 377292 reaction equation
Br.[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:16]4[CH:17]=[C:18]5[C:22](=[C:23]([F:25])[CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:13]=3[CH3:15])[C:8](=[O:26])[C:7]([C:27]([OH:29])=[O:28])=[CH:6]2)[CH2:4][CH2:3]1>C(O)C.[OH-].[Na+]>[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:16]4[CH:17]=[C:18]5[C:22](=[C:23]([F:25])[CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:13]=3[CH3:15])[C:8](=[O:26])[C:7]([C:27]([OH:29])=[O:28])=[CH:6]2)[CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 70111644HCID 70111644, compound

Product 1

HCID 15458203HCID 15458203, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 3.0 ml of 47% hydrobromic acid was suspended 0.30 g of 1-cyclopropyl-7-[7-fluoro-2-(p-toluenesulfonyl)isoindolin-5-yl]-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, followed by adding thereto 0.16 g of phenol and 1.8 ml of propionic acid, and the resulting mixture was heated at 100° C. for 10 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, after which ethanol was added to the resulting residue and the crystals were collected by filtration to obtain 0.21 g of colorless 1-cyclopropyl-7-(7-fluoroisoindolin-5-yl)-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrobromide. The hydrobromide obtained was suspended in 1.3 ml of ethanol and dissolved in 2.6 ml of a 0.5 N aqueous sodium hydroxide solution, after which carbon dioxide was bubbled into the resulting solution and the crystals were collected by filtration to obtain 0.10 g of colorless 1-cyclopropyl-7-(7-fluoroisoindolin-5-yl)-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. customafter which carbon dioxide was bubbled into the resulting solution
  2. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-b4010c69600a46dda692039cab3ca0a8
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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