HCID 15676980, compound → 5-Hydroxy-8-methoxy-3,4-dihydroquinolin-2(1H)-one

HRID 1090703Notes

Reaction equation

HRID 1090703 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:14])[NH:7]2.[H][H]>CN1CCCC1=O.[OH-].[Pd+2].[OH-]>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:14])[NH:7]2

Participants

5

Reactant 2

HCID 15676980HCID 15676980, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 130525825-Hydroxy-8-methoxy-3,4-dihydroquinolin-2(1H)-oneYield 98.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-Hydroxy-8-methoxycarbostyril (12.5 g) in 200 ml of N-methylpyrrolidinone with 500 mg of palladium hydroxide (20%) were hydrogenated at 50° C. under 1,2 bar hydrogen. The catalyst was removed by filtration through Celite and the solvent evaporated to give 12.4 g of 5-hydroxy-8-methoxy-3,4-dihydrocarbostyril (mp=190° C.).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-512605e9886648c884bdce630c49e498
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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