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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 7492Generated: October 25, 2026

5-Amino-4-fluoro-2-methylphenol → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

https://huagongshe.com/reaction/7492

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Amino-4-fluoro-2-methylphenolHCID 10154098—
Reactant4-Chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochlorideHCID 21991011—
Solvent2-PentanolHCID 22386—
Product4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochlorideHCID 2199105529.3%

Reaction Steps

A solution of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (268 mg, 0.71 mmol), (prepared as described for the starting material in Example 10), and 2-fluoro-5-hydroxy-4-methylaniline, (109 mg, 0.77 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (6 ml) was heated at reflux for 4 hours. After dilution with isopropanol the solid was filtered off, washed with isopropanol followed by ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (92 mg, 29%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07087602B2
Source datasetuspto-grants-2006_08
ORD IDord-ede3ca8d119b49a8ac2e73f1d9c835b8
Source noteuspto-grants-2006_08