1,6-Dibromohexane → 2-[3-[(6-Bromohexyl)oxy]propyl]quinoline

HRID 1886033Notes

Reaction equation

HRID 1886033 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][OH:14].[OH-].[Na+].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>O.CCOCC>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:14][CH2:13][CH2:12][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 218061343-(Quinolin-2-yl)propan-1-ol

Product 1

HCID 198767552-[3-[(6-Bromohexyl)oxy]propyl]quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2-Quinolinepropanol (0.92 g), 50% aqueous sodium hydroxide (5 ml), 1,6-dibromohexane (5 ml) and TAB (57 mg) were vigorously stirred at 21° for 6 h. The mixture was diluted with water (25 ml) and ether (100 ml) and the organic phase dried and evaporated in vacuo. The residue was purified by FCC with hexane eluant to remove 1,6-dibromohexane. Elution with ether afforded the title compound as a yellow oil (0.88 g), t.l.c. ether Rf 0.51.

Workup

  1. customthe organic phase dried
  2. customevaporated in vacuo
  3. customThe residue was purified by FCC with hexane eluant
  4. customto remove 1,6-dibromohexane
  5. washElution with ether

Sources & evidence

ORD record
ord-72fc97cfd6b24beeb8cfedffad248d1c
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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