Isoquinoline → HCID 11786613, compound

HRID 1036586Notes

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

Participants

Reactant 2

HCID 8405Isoquinoline

HCID 187661,12-Dibromododecane

Product 1

HCID 11786613HCID 11786613, compound

Conditions

Temperature: 65 °C

Procedure

1,12-Dibromododecane (mmol) was added to a solution (30 mL) of isoquinoline, 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 off-white solid was isolated. 1H NMR (300 MHz, DMSO-D6) δ 10.06 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.35 (1H, d, C7-H), 8.25 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.70 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.75 (1H, m, C′3-CH2), 1.15-1.40 (7H, m, C′3-6-CH2).

Workup

filtrationThe resulting precipitate was filtered
washthe product washed five times with dry diethyl ether
customThe resulting off-white solid was isolated

Sources & evidence

ORD record: ord-66820bf80d4e4370b75982c01524f75b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546415B2

Reaction notes

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