Quinoline → 1-(2-Bromoethyl)quinolin-1-ium bromide

HRID 596143Notes

Reaction equation

HRID 596143 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:11][CH2:12][CH2:13]Br>>[Br-:11].[Br:11][CH2:12][CH2:13][N+:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 7047QuinolineHCID 78391,2-Dibromoethane

Product 1

HCID 114043161-(2-Bromoethyl)quinolin-1-ium bromide

Procedure

A solution of quinoline (20 ml) in 200 ml of 1,2-dibromoethane was heated under nitrogen at 70° C. for 18 hours. The crystalline solid was filtered, washed with dichloromethane and recrystallized from methanol-ether. Collected 32 g (65 per cent yield) m.p. 205°-207° C. Nmr (D2O) 4.22 (t, 2), 5.63 (t, 2), 7.8 - 8.6 (m, 5), 9.1 - 9.6 (m, 3).

Workup

  1. filtrationThe crystalline solid was filtered
  2. washwashed with dichloromethane
  3. customrecrystallized from methanol-ether
  4. customCollected
  5. custom32 g (65 per cent yield) m.p. 205°-207° C

Sources & evidence

ORD record
ord-df4bda40b5be4684a1661a43baeeb9d2
Source dataset
uspto-grants-1977_03
Patent number
US04010156

Reaction notes

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