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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851403Generated: November 2, 2026

Dimethylformamide → ethyl 7-amino-6-chloro-1H-indole-2-carboxylate

https://huagongshe.com/reaction/1851403

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantChlorosuccinimideHCID 31398—
Reactant1H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 11138194—
SolventWaterHCID 962—
Productethyl 7-amino-6-chloro-1H-indole-2-carboxylateHCID 5747602363.5%

Reaction Steps

A mixture of ethyl 7-amino-1H-indole-2-carboxylate (2.30 g), N-chlorosuccinimide (1.40 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature overnight. To the reaction mixture was added water, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.59 g, yield 63%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 217-218° C. (decomposition).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957070B2
Source datasetuspto-grants-2015_02
ORD IDord-6f1904cf21a14c158381805d829b408c
Source noteuspto-grants-2015_02