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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2261842Generated: November 3, 2026

Acetic Acid → methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

https://huagongshe.com/reaction/2261842

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant2-(4-Chloro-2-nitro-phenyl)-3-hydroxy-but-2-enoic acid methyl esterHCID 58771141—
CatalystIronHCID 23925—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Productmethyl 6-chloro-2-methyl-1H-indole-3-carboxylateHCID 57443356—

Reaction Conditions

Temperature115 °C

Reaction Steps

A mixture of 2-(4-chloro-2-nitro-phenyl)-3-hydroxy-but-2-enoic acid methyl ester (4.66 g, 17.2 mmol), iron (5.76 g, 103 mmol) and glacial acetic acid (16 mL) is heated at 115° C. for 1 h and allowed to cool. The reaction mixture is diluted with water and ethyl acetate. The ethyl acetate layer is washed with brine and dried over MgSO4. The mixture of the title compound and a small amount of impurity is used in the next reaction without additional purification. ES/MS m/e 224.0 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07846960B2
Source datasetuspto-grants-2010_12
ORD IDord-3e5d8346ee0f406cb3c0927a0c99d60f
Source noteuspto-grants-2010_12