Quinoline → 1,9-Di(1-Quinoliniumyl)Nonane With Dibromide Ions

HRID 1036580Notes

Reaction equation

HRID 1036580 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>>[Br-:1].[Br-:1].[CH2:2]([N+:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N+:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7047QuinolineHCID 206771,9-Dibromononane

Product 1

HCID 113647651,9-Di(1-Quinoliniumyl)Nonane With Dibromide IonsYield 92%

Conditions

Temperature
65 °C

Procedure

1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry quinoline, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting purple solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.68 (1H, d, C2-H), 9.34 (1H, d, C3-H), 8.67 (1H, d, C8-H), 8.55 (1H, d, C4-H), 8.27 (2H, m, C5&C7-H), 8.07 (1H, d, C6-H), 5.09 (2H, t, C′1-CH2), 1.95 (2H, m, C′2-CH2), 1.19-1.45 (5H, m, C′3-5-CH2).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthe product washed five times with dry diethyl ether
  3. customThe resulting purple solid was isolated in a 92% yield

Sources & evidence

ORD record
ord-6e0fa1daeb2341a389fffb62171a2c83
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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