Cyclohexene → HCID 59527116, compound

HRID 384439Notes

Reaction equation

HRID 384439 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH:19]=[CH:20][CH2:21][CH2:22][O:23]CC2C=CC=CC=2)[C:10]=1[CH3:31])C1C=CC=CC=1.C1CCCCC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][C:11]1[NH:12][C:13]2[C:18]([C:9](=[O:8])[C:10]=1[CH3:31])=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 68506455HCID 68506455, compound

Product 1

HCID 59527116HCID 59527116, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(benzyloxy)-2-[4-(benzyloxy)-1-buten-1-yl]-3-methylquinoline (2.57 g) in ethanol (26 mL) were added cyclohexene (13 mL) and 20% palladium hydroxide-activated carbon powder (1.5 g), followed by stirring under reflux for 2 hours. The catalyst was removed by filtration, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=93/7) to obtain 2-(4-hydroxybutyl)-3-methylquinolin-4(1H)-one (1.10 g).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=93/7)

Sources & evidence

ORD record
ord-33ab354d4a38447ab436b529af71bb78
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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