Carbon Dioxide → HCID 15870848, compound

HRID 1584831Notes

Reaction equation

HRID 1584831 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:35])=[C:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][N:20](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:19]5)[C:12]=3[O:14]C)[C:7](=[O:36])[C:6]([C:37]([OH:39])=[O:38])=[CH:5]2)[CH2:3][CH2:2]1.C1(O)C=CC=CC=1.C(O)(=O)CC.[OH-].[Na+].C(=O)=O>Br.O.C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:35])=[C:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[CH2:21][NH:20][CH2:19]5)[C:12]=3[OH:14])[C:7](=[O:36])[C:6]([C:37]([OH:39])=[O:38])=[CH:5]2)[CH2:2][CH2:3]1

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 996PhenolHCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 21220218HCID 21220218, compound

Product 1

HCID 15870848HCID 15870848, compound

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

In 0.5 ml of 47% hydrobromic acid was suspended 50 mg of 1-cyclopropyl-6-fluoro-8-methoxy-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, and to the suspension were added 26 mg of phenol and 0.3 ml of propionic acid, after which the resulting mixture was stirred at 130° C. for six hours. The reaction mixture was concentrated under reduced pressure, and to the residue obtained were added 0.3 ml of ethanol, 0.3 ml of 1N aqueous sodium hydroxide solution and 0.3 ml of water to dissolve the residue. Thereafter, a carbon dioxide gas was blown into the solution, and the crystals precipitated were collected by filtration, to obtain 12 mg of pale yellow, crystalline 1-cyclopropyl-6-fluoro-8-hydroxy-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto the residue obtained
  3. dissolutionto dissolve the residue
  4. customthe crystals precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1567a22419e44d878a06d2bec9783e4f
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

Loading…