Quinoline → HCID 11490183, compound

HRID 1036582Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>>[Br-:1].[Br-:1].[CH2:2]([N+:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N+:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 7047Quinoline

HCID 187661,12-Dibromododecane

Product 1

HCID 11490183HCID 11490183, compoundYield 92%

Conditions

Temperature: 65 °C

Procedure

1,12-Dibromododecane (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 a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.58 (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), 8.04 (1H, d, C6-H), 5.04 (2H, t, C′1-CH2), 1.95 (2H, m, C′2-CH2), 1.2-1.4 (8H, m, C′3-6-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, 28.9, 28.8, 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 a 92% yield

Sources & evidence

ORD record: ord-e2e3ac97593f4c2aa953dc470c4d7ec9
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546415B2

Reaction notes

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