2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinoline → 2-[6-[(6-Bromohexyl)oxy]hexyl]quinoline

HRID 1088715Notes

Reaction equation

HRID 1088715 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>C(O)C.[Pd]>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

4

Reactant 1

HCID 198767592-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinoline

Product 1

HCID 221617372-[6-[(6-Bromohexyl)oxy]hexyl]quinolineYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[6-[(6-bromohexyl)oxy]-1-hexynyl]quinoline (2.29 g) in ethanol (120 ml) was hydrogenated at room temperature and pressure over pre-reduced 10% palladium on carbon (1 g) for 20 min. The catalyst was removed by filtration through hyflo and the filtrate evaporated in vacuo to a brown oil. Purification by FCC eluting with hexane-ether (2:1) gave the title compound as a pale brown oil (1.70 g), t.l.c. (hexane:ether 2:1) Rf 0.21.

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration through hyflo
  3. customthe filtrate evaporated in vacuo to a brown oil
  4. customPurification by FCC
  5. washeluting with hexane-ether (2:1)

Sources & evidence

ORD record
ord-76eac424e8314a9f9f41d04ae64f749b
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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