Quinoline → 1,8-Di(1-Quinoliniumyl)Octane With Diiodide Ions

HRID 1036579Notes

Reaction equation

[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]I.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>>[I-:1].[I-:1].[CH2:2]([N+:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 7047Quinoline

HCID 906051,8-Diiodooctane

Product 1

HCID 114449851,8-Di(1-Quinoliniumyl)Octane With Diiodide IonsYield 89%

Conditions

Temperature: 65 °C

Procedure

1,8-Diiodooctane (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 yellow solid was isolated in an 89% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.53 (1H, d, C2-H), 9.29 (1H, d, C3-H), 8.61 (1H, d, C8-H), 8.50 (1H, d, C4-H), 8.29 (1H, t, C7-H), 8.18 (1H, t, C5-H), 8.07 (1H, d, C6-H), 5.09 (2H, t, C′1-CH2), 1.96 (2H, m, C′2-CH2), 1.25 (4H, m, C′3&4-CH2); 13C NMR (75 MHz, DMSO-D6) δ 149.5, 147.4, 137.4, 135.6, 130.7, 129.9, 129.7, 122.1, 118.9, 57.3, 29.5, 28.5, 25.7.

Workup

filtrationThe resulting precipitate was filtered
washthe product washed five times with dry diethyl ether
customThe resulting yellow solid was isolated in an 89% yield

Sources & evidence

ORD record: ord-bab84625244742d38da121ab953f21e2
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546415B2

Reaction notes

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