5-Methoxy-2,3,3-trimethyl-3H-indole → HCID 86637540, compound

HRID 389241

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-586ad7d3615349a1a9ad3d8ba7246df2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378120B2

Linked notes

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