5-Methoxy-2,3,3-trimethyl-3H-indole → 1-(3,5-dinitrobenzyl)-5-methoxy-2,3,3-trimethyl-3H-indolium iodide

HRID 2105101Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]2([CH3:14])[CH3:13].[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[CH2:21][I:22])([O-:17])=[O:16]>ClC1C=CC=CC=1Cl>[I-:22].[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:26]([O-:28])=[O:27])[CH:25]=1)[CH2:21][N+:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[C:6]([CH3:14])([CH3:13])[C:7]=1[CH3:12])([O-:17])=[O:16]

Participants

Conditions

Temperature: 75 °C

Procedure

To 5-methoxy-2,3,3-trimethyl-3H-indole (1.90 g) was added 3,5-dinitrobenzyl iodide (4.62 g) and 1,2-dichlorobenzene (10 ml). The mixture was heated at 75° C. for 3 hours, during which time an orange solid separated. The mixture was then cooled in an ice bath and the solid fraction collected by filtration; it was washed sequentially with dichlorobenzene and diethyl ether and dried under vacuum to give the product (2.62 g).

Workup

customseparated
temperatureThe mixture was then cooled in an ice bath
filtrationthe solid fraction collected by filtration
washit was washed sequentially with dichlorobenzene and diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-ed7bc65f4bc0467ca5bdcf6257ecb444
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579140B2

Reaction notes

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