Indole → 1-[(4-Nitrophenyl)methyl]-1H-indole

HRID 2303386Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1)([O-:14])=[O:13]>CS(C)=O>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4]2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 5.28 g of sodium hydride (0.22 mol, mineral oil suspension) in 200 ml of dimethyl sulfoxide is treated with a solution of 23.4 g (0.2 mol) of indole in 100 ml of dimethyl sulfoxide. It is heated at 65° C. for 1 hour, then allowed to cool and 37.7 g (0.22 mol) of 4-nitrobenzyl chloride are then added dropwise. The solution is heated to 60° C., kept at room temperature for 14 hours and then poured into 700 ml of ater with stirring. The mixture is extracted in portions with a total of 300 ml of methylene chloride, the organic phase is dried using anhydrous sodium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified on a silica gel column (silica gel 60, Merck AG, Darmstadt; eluent methylene chloride/ethanol 9:1, v/v).

Workup

temperatureto cool
temperatureThe solution is heated to 60° C.
additionpoured into 700 ml of ater
extractionThe mixture is extracted in portions with a total of 300 ml of methylene chloride
customthe organic phase is dried
filtrationfiltered
concentrationthe filtrate is concentrated in vacuo
customThe residue is purified on a silica gel column (silica gel 60, Merck AG, Darmstadt

Sources & evidence

ORD record: ord-ac9dc70d65a549738a824bc0ae7f2c70
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06432987B1

Reaction notes

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