Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 387860Generated: October 25, 2026

Dimethylformamide → Methyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylate

https://huagongshe.com/reaction/387860

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium hydrideHCID 24758—
Reactant4-Amino-3-chlorophenolHCID 87184—
ReactantMethyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylateHCID 22936872—
SolventWaterHCID 962—
ProductMethyl 4-(4-amino-3-chlorophenoxy)-7-(2-methoxyethoxy)-6-quinolinecarboxylateHCID 22936947—

Reaction Steps

Methyl 4-chloro-7-(2-methoxyethoxy)-6-quinolinecarboxylate (4.9 g), 4-amino-3-chlorophenol (2.0 g), sodium hydride (550 mg) and dimethylformamide (20 ml) were stirred together at 100° C. for 2 hours. The mixture was returned to room temperature, water was added, and extraction was performed with ethyl acetate. Silica gel was added to the extract solution and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate) to obtain 3.2 g of the target substance as a violet solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08372981B2
Source datasetuspto-grants-2013_02
ORD IDord-b4d87319d2d54138b953708e9b2426b0
Source noteuspto-grants-2013_02