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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 720333Generated: October 27, 2026

Methyl iodide → methyl N-methyl-4,5,6-trimethoxyindole-2-carboxylate

https://huagongshe.com/reaction/720333

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
Reactant18-Crown-6HCID 28557—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantMethyl 3-(2,3,4-trimethoxyphenyl)-2-azidopropenoateHCID 86587494—
SolventBenzeneHCID 241—
SolventWaterHCID 962—
Productmethyl N-methyl-4,5,6-trimethoxyindole-2-carboxylateHCID 21891561—

Reaction Steps

Methyl 3-(2,3,4-trimethoxyphenyl)-2-azidopropenoate (799 mg), potassium tert-butoxide (438 mg) and 18-crown-6(71 mg) were dissolved in dry benzene (60 mL), and the solution was stirred for 15 minutes. Iodomethane (0.28 mL) was then added, and the mixture was stirred overnight. Water was added to the reaction mixture to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07135473B2
Source datasetuspto-grants-2006_11
ORD IDord-d996a062b151461d9f4e7f84c0228c9b
Source noteuspto-grants-2006_11