HCID 68508420, compound → HCID 59527569, compound

HRID 384483Notes

Reaction equation

HRID 384483 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][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]=1[CH3:32])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[F:31][C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:11]2[NH:12][C:13]3[C:18]([C:9](=[O:8])[C:10]=2[CH3:32])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 68508420HCID 68508420, compound

Product 1

HCID 59527569HCID 59527569, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

4-(Benzyloxy)-2-[5-(4-fluorophenoxy)pent-1-en-1-yl]-3-methylquinoline (E/Z mixture, 810 mg) was dissolved in ethanol-THF (1:1, 20 mL), and 10% palladium-activated carbon (200 mg) was added thereto. The mixture was stirred at room temperature under hydrogen atmosphere for 3 hours. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 2-[5-(4-fluorophenoxy)pentyl]-3-methylquinolin-4(1H)-one (572 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-1e6b184728fb4ebe9cb0560b2a017c03
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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