2-Hydroxyquinoline → Hydrocarbostyril

HRID 1090690Notes

Reaction equation

HRID 1090690 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:2]1=[O:3].[H][H]>CO.C(O)(=O)C.CN1CCCC1=O.[OH-].[Pd+2].[OH-]>[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3]

Participants

6

Reactant 2

HCID 60382-HydroxyquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 64796Hydrocarbostyril

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 13387N-methyl-2-pyrrolidoneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

A carbostyril of Formula 14 is hydrogenated, e.g., in a mixture of methanol/acetic acid, or preferably in N-methylpyrrolidinone, with a palladium hydroxide catalyst at elevated temperature (e.g., 40° to 80° C.) and under a source of hydrogen for 24 to 48 hours, preferably about 36 hours. The catalyst is removed to give the 3,4-dihydrocarbostyril compound of Formula 5c.

Workup

  1. custompreferably about 36 hours
  2. customThe catalyst is removed

Sources & evidence

ORD record
ord-b8999b2b4df24a70993693a9f20129ee
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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