Dichloromethane → 2-[2-[(6-Bromohexyl)oxy]ethyl]quinoline

HRID 1088706Notes

Reaction equation

HRID 1088706 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][OH:13].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[OH-].[Na+].ClCCl>O.CCOCC>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O: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

7

Reactant 4

HCID 6344DichloromethaneHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 705322-Quinolineethanol

Product 1

HCID 221617492-[2-[(6-Bromohexyl)oxy]ethyl]quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-quinolineethanol (1.00 g), 1,6-dibromohexane (4 ml), TAB (100 mg), 50% aqueous sodium hydroxide (4 ml) and dichloromethane (3 ml) was stirred at room temperature for 40 h, then diluted with water (40 ml) and ether (25 ml). The organic phase was washed with water (20 ml), dried and evaporated in vacuo. The residual oil was purified by FCC eluting with hexane followed by hexane-ether (9:1) and ether, to give the title compound (1.18 g) as a pale yellow oil, t.l.c. (diethyl ether) Rf 0.44.

Workup

  1. washThe organic phase was washed with water (20 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customThe residual oil was purified by FCC
  5. washeluting with hexane

Sources & evidence

ORD record
ord-7431bd3e640a4eb8959f2b7909f12814
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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