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

HRID 982398Notes

Reaction equation

HRID 982398 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[CH:25]>C(#N)C.CCOCC.[Cu]I>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[C:25][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 2

HCID 27627562-BromoquinolineHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Product 1

HCID 198767592-[6-[(6-Bromohexyl)oxy]-1-hexynyl]quinolineYield 75.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromoquinoline (3.00 g), 6-[(6-bromohexyl)oxy]-1-hexyne (3.77 g), BTPC (90 mg), copper (I) iodide (11 mg) and dicyclohexyamine (2.79 g) in acetonitrile (35 ml) was stirred at room temperature under nitrogen for 20 h. The mixture was diluted with ether (90 ml), filtered and the filtrate evaporated in vacuo to give a brown oil. Purification by FCC eluting with hexane:ether (4:1→2:1) gave the title compound as a brown oil (4.25 g), t.l.c. (hexane:ether 2:1) Rf 0.22.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated in vacuo
  3. customto give a brown oil
  4. customPurification by FCC
  5. washeluting with hexane:ether (4:1→2:1)

Sources & evidence

ORD record
ord-7d8f56412161427a9ffb1e274a6caf0a
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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