Isoquinoline → HCID 11787103, compound

HRID 1036585Notes

Reaction equation

[I:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]I.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1>>[I-:1].[I-:1].[CH2:2]([N+:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N+:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1

Participants

Reactant 2

HCID 8405Isoquinoline

HCID 85378Decane, 1,10-diiodo-

Product 1

HCID 11787103HCID 11787103, compoundYield 92%

Conditions

Temperature: 65 °C

Procedure

1,10-Diiododecane (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 yellow solid was isolated in a 92% yield. 1H NMR (300 MHz, DMSO-D6) δ 10.07 (1H, d, C1-H), 8.78 (1H, d, C3-H), 8.58 (1H, d, C8-H), 8.48 (1H, d, C4-H), 8.36 (1H, d, C7-H), 8.26 (1H, t, C5-H), 8.07 (1H, t, C6-H), 4.69 (2H, t, C′1-CH2), 2.0 (2H, m, C′2-CH2), 1.15-1.50 (6H, m, C′3-5-CH2).

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-e731bab0088d48219dc5f08a065bd420
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546415B2

Reaction notes

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