Hydrochloric Acid → HCID 19592340, compound

HRID 613578Notes

Reaction equation

HRID 613578 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O:22]C)=[O:21])[CH:15]=1.[OH-].[Na+].Cl>CO.O1CCOCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19592861HCID 19592861, compound

Product 1

HCID 19592340HCID 19592340, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-bromo-8-[3-(methoxycarbonyl)benzoylamino]quinoline (356 mg) and 1N sodium hydroxide aqueous solution (1.1 ml) in methanol (5 ml) and dioxane (5 ml) was gently refluxed for 2 hours. After cooling, the mixture was neutralized with 1N hydrochloric acid. The solvent was removed in vacuo, and the residue was washed with hot 95% ethanol and collected by filtration to give 3-bromo-8-(3-carboxybenzoylamino)quinoline (397 mg) as pale tan solid.

Workup

  1. temperaturewas gently refluxed for 2 hours
  2. temperatureAfter cooling
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with hot 95% ethanol
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f3f9aa8daf61462f851e664e550fec62
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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