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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2191675Generated: November 1, 2026

Citric Acid → HCID 57668103, compound

https://huagongshe.com/reaction/2191675

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
Reactant4-MethylmorpholineHCID 7972—
Reactant8-AminoquinolineHCID 11359—
ReactantHCID 57667966HCID 57667966—
CatalystCopperHCID 23978—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 57668103HCID 5766810316.3%

Reaction Conditions

Temperature90 °C

Reaction Steps

To N,N-dimethylformamide 8.8 mL solution of 2-iodo-4-phenoxybenzoic acid 0.88 g were added quinolin-8-amine 0.75 g, N-methylmorpholine 0.85 mL, copper(I) iodide 0.15 g and copper powder 49 mg, and it was stirred at 90° C. for 6 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it, it was adjusted to pH6.5 with 10% citric acid aqueous solution, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to give 4-phenoxy-2-(quinolin-8-ylamino)benzoic acid 0.15 g of pale yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08327467B2
Source datasetuspto-grants-2012_12
ORD IDord-d488b13482564bcbb3682ebd9a0a7ef2
Source noteuspto-grants-2012_12