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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1865202Generated: October 31, 2026

Ethyl 5-hydroxy-1H-indole-2-carboxylate → HCID 57756359, compound

https://huagongshe.com/reaction/1865202

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl 5-hydroxy-1H-indole-2-carboxylateHCID 90677—
Reactant4-Chloro-6,7-dimethoxyquinolineHCID 459610—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
ProductHCID 57756359HCID 57756359—

Reaction Conditions

Temperature180 °C

Reaction Steps

A mixture of 4-chloro-6,7-dimethoxy-quinoline (0.4 g, 1.8 mmol), 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (0.37 g, 1.8 mmol, Biosynth AG) and DMAP (0.22 g, 1.8 mmol, Aldrich) in toluene (in a microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 180° C. for 2 h. The mixture was cooled to RT and diluted with 30 mL of EtOAc. The solution was washed with 10 mL of brine twice, dried over Na2SO4 and concentrated in vacuo. The residue was further purified with silica gel column chromatography (50% to 100% EtOAc in hexanes) to provide a white foam as the desired compound. MS (ESI pos. ion) m/z: 393 (M+H). Calc'd Exact Mass for C22H20N2O5: 392.40.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07626030B2
Source datasetuspto-grants-2009_12
ORD IDord-b42fdbfe91234204a296d9c6a53048c1
Source noteuspto-grants-2009_12