Chloroform → HCID 19914474, compound

HRID 1090124Notes

Reaction equation

HRID 1090124 reaction equation
C([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:21])[CH:12]=[CH:13][NH:14]2)C1C=CC=CC=1.[H][H].C(Cl)(Cl)[Cl:25]>CO.[C].[Pd]>[ClH:25].[OH:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:21])[CH:12]=[CH:13][NH:14]2

Participants

6

Reactant 3

HCID 6212ChloroformHCID 15675232HCID 15675232, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19914474HCID 19914474, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In a mixed solvent of methanol (9 ml) and chloroform (1 ml) was dissolved 5-benzyloxy-6-methoxy-4(1H)-quinolone (120 mg). To this solution was added 10% palladium-carbon (50 mg), and the mixture was stirred under a stream of hydrogen at room temperature for 2 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The crude product thus obtained was recrystallized from chloroform-methanol-n-hexane to obtain 5-hydroxy-6-methoxy-4(1H)-quinolone hydrochloride (a salt of compound 1, 73 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product thus obtained
  4. customwas recrystallized from chloroform-methanol-n-hexane

Sources & evidence

ORD record
ord-6daa01fed04242138e952fd2445a5ae7
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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